# Patent

## Title
Compound for an organic optoelectronic device, organic light emitting diode including the same, and display including the organic light emitting diode

## Abstract

A compound for an organic optoelectronic device, an organic light emitting diode, and a display device, the compound being represented by the following Chemical Formula 1:

## Background
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of pending International Application No. PCT/KR2011/003224 entitled “Compound for Organic Optoelectronic Device, Organic Light Emitting Diode Including the Same and Display Including the Organic Light Emitting Diode,” which was filed on Apr. 29, 2011, the entire contents of which are hereby incorporated by reference.
Korean Patent Application No. 10-2010-0140563, filed on Dec. 31, 2010, in the Korean Intellectual Property Office, and entitled: “Compound for Organic Optoelectronic Device, Organic Light Emitting Diode Including the Same and Display Including the Organic Light Emitting Diode,” is incorporated by reference herein in its entirety.


BACKGROUND
1. Field
Embodiments relate to a compound for an organic optoelectronic device, an organic light emitting diode including the same, and a display including the organic light emitting diode.
2. Description of the Related Art
An organic optoelectronic device is, in a broad sense, a device for transforming photo-energy to electrical energy, or conversely, a device for transforming electrical energy to photo-energy.
An organic optoelectronic device may be classified as follows in accordance with its driving principles. One type of organic optoelectronic device is an electronic device driven as follows: excitons may be generated in an organic material layer by photons from an external light source; the excitons may be separated into electrons and holes; and the electrons and holes may be transferred to different electrodes as a current source (voltage source).
Another type of organic optoelectronic device is an electronic device driven as follows: a voltage or a current may be applied to at least two electrodes to inject holes and/or electrons into an organic material semiconductor positioned at an interface of the electrodes, and the device may be driven by the injected electrons and holes.
Examples of an organic optoelectronic device may include an organic photoelectric device, an organic solar cell, an organic photo conductor drum, and an organic transistor, and it requires a hole injecting or transporting material, an electron injecting or transporting material, or a light emitting material.
An organic light emitting diode (OLED) has recently drawn attention due to an increase in demand for flat panel displays. In general, organic light emission may refer to transformation of electrical energy to photo-energy.
SUMMARY
Embodiments are directed to a compound for an organic optoelectronic device, an organic light emitting diode including the same, and a display including the organic light emitting diode
The embodiments may be realized by providing a compound for an organic optoelectronic device, the compound being represented by the following Chemical Formula 1:




wherein, in Chemical Formula 1 X1 and X2 are each independently —N— or —CR′—, in which R′ is hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof, or forms a sigma bond with one of the *, R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof, Ar1 to Ar3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, L1 to L3 are each independently a single bond, a substituted or unsubstituted C2 to C6 alkenyl group, a substituted or unsubstituted C2 to C6 alkynyl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof, and n, m, and o are each independently 0 or 1.
The compound may be represented by the following Chemical Formula 2:




wherein, in Chemical Formula 2 X1 is —N— or —CR′—, in which R′ is hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof, R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof, Ar1 to Ar3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, L1 to L3 are each independently a single bond, a substituted or unsubstituted C2 to C6 alkenyl group, a substituted or unsubstituted C2 to C6 alkynyl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof, and n, m, and o are each independently 0 or 1.
X1 may be N. At least one of Ar1 or Ar2 may be a substituted or unsubstituted C3 to C30 heteroaryl group.
Ar1 may be a substituted or unsubstituted C3 to C30 heteroaryl group, and Ar2 and Ar3 may each independently be a substituted or unsubstituted C6 to C30 aryl group.
Ar2 may be a substituted or unsubstituted C3 to C30 heteroaryl group, and Ar1 and Ar3 may each independently be a substituted or unsubstituted C6 to C30 aryl group.
The substituted or unsubstituted C3 to C30 heteroaryl group may be a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted oxatriazolyl group, a substituted or unsubstituted thiatriazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphpyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, or a combination thereof.
The substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triperylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, or a combination thereof.
The embodiments may also be realized by providing a compound for an organic optoelectronic device, the compound being represented by one of the following Chemical Formulae A1 to A189:




























































































































































































































The embodiments may also be realized by providing a compound for an organic optoelectronic device, the compound being represented by one of the following Chemical Formulae B1 to B175:























































































































































































































































The embodiments may also be realized by providing a compound for an organic optoelectronic device, the compound being represented by one of the following Chemical Formulae C1 to C173:

















































































































































































































































The organic optoelectronic device may be selected from the group of an organic photoelectric device, an organic light emitting diode, an organic solar cell, an organic transistor, an organic photo conductor drum, and an organic memory device.
The embodiments may also be realized by providing an organic light emitting diode including an anode, a cathode, and at least one thin layer between the anode and the cathode, wherein the at least one organic thin layer includes the compound for an organic optoelectronic device according to an embodiment.
The at least one organic thin layer may be selected from the group of an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking layer, and a combination thereof.
The at least one organic thin layer may include an electron transport layer (ETL) or an electron injection layer (EIL), and the compound for an organic optoelectronic device may be included in the electron transport layer (ETL) or the electron injection layer (EIL).
The at least one organic thin layer may include an emission layer, and the compound for an organic optoelectronic device may be included in the emission layer.
The at least one organic thin layer may include an emission layer, and the compound for an organic optoelectronic device may be a phosphorescent or fluorescent host material in the emission layer.
The at least one organic thin layer may include an emission layer, and the compound for an organic optoelectronic device may be a fluorescent blue dopant material in the emission layer.
The embodiments may also be realized by providing a display device including the organic light emitting diode according to an embodiment.



BRIEF DESCRIPTION OF THE DRAWINGS
Features will become apparent to those of ordinary skill in the art by describing in detail exemplary embodiments with reference to the attached drawings in which:
FIGS. 1 to 5 illustrate cross-sectional views showing organic optoelectronic devices according to various embodiments.



DETAILED DESCRIPTION
Example embodiments will now be described more fully hereinafter with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.
In the drawing figures, the dimensions of layers and regions may be exaggerated for clarity of illustration. It will also be understood that when a layer or element is referred to as being “on” another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being “between” two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Like reference numerals refer to like elements throughout.
As used herein, when specific definition is not otherwise provided, the term “substituted” refers to one substituted with a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C10 alkoxy group, a fluoro group, a C1 to C10 trifluoro alkyl group such as trifluoromethyl group, or a cyano group.
As used herein, when specific definition is not otherwise provided, the term “hetero” refers to one including 1 to 3 hetero atoms selected from the group of N, O, S, and P, and remaining carbons in one functional group.
As used herein, when a definition is not otherwise provided, the term “combination thereof” refers to at least two substituents bound to each other by a linker, or at least two substituents condensed to each other.
As used herein, when a definition is not otherwise provided, the term “alkyl” refers to an aliphatic hydrocarbon group. The alkyl group may be a “saturated alkyl group” that does not include a double bond or a triple bond.
The alkyl group may be an “unsaturated alkyl group” including at least one alkenyl group or alkynyl group. Regardless of being saturated or unsaturated, the alkyl may be branched, linear, or cyclic.
The alkyl group may be a C1 to C20 alkyl group. The alkyl group may be a C1 to C10 medium-sized alkyl group. The alkyl group may be a C1 to C6 lower alkyl group.
For example, a C1 to C4 alkyl group may have 1 to 4 carbon atoms and may be selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and t-butyl.
Examples of an alkyl group may be selected from the group of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, an ethenyl group, a propenyl group, a butenyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
The term “aromatic group” may refer a functional group including a cyclic structure where all elements have p-orbitals which form conjugation. Specific examples include an aryl group and a heteroaryl group.
The term “aryl” may refer to a monocyclic or fused ring-containing polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) groups.
The “heteroaryl group” may refer to one including 1 to 3 heteroatoms selected from the group of N, O, S, and P in an aryl group, and remaining carbons.
The term “spiro structure” refers to a cyclic structure having a contact point of one carbon. Further, the spiro structure may be used as a compound including the spiro structure or a substituent including the Spiro structure.
According to an embodiment, a compound for an organic optoelectronic device represented by the following Chemical Formula 1 is provided.




In Chemical Formula 1, X1 and X2 may each independently be —N— or —CR′—. R′ may be a sigma bond with one of the *, or may be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof. R1 and R2 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof. Ar1 to Ar3 may each independently be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group. L1 to L3 may each independently be a single bond, a substituted or unsubstituted C2 to C6 alkenyl group, a substituted or unsubstituted C2 to C6 alkynyl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof. n, m, and may each independently be 0 or 1.
In an implementation, the compound for an organic optoelectronic device represented by the above Chemical Formula 1 may include a fused ring core including a nitrogen atom and three substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups.
In an implementation, the compound represented by the above Chemical Formula 1 may be a compound represented by the following Chemical Formula 2.




In Chemical Formula 2, X1 may be —N— or —CR′—. R′ may be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof. R1 and R2 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof. Ar1 to Ar3 may each independently be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group. L1 to L3 may each independently be a single bond, a substituted or unsubstituted C2 to C6 alkenyl group, a substituted or unsubstituted C2 to C6 alkynyl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof n, m, and o may each independently be 0 or 1.
The compound represented by Chemical Formula 2 may be easily synthesized, may have an asymmetric structure that is not easily crystallized in a device, and may have high thermal stability due to a bulk core.
In an implementation, the fused ring core may include at least one nitrogen atom. In an implementation, the fused ring core may include one or two nitrogen atoms. For example, in Chemical Formula 2, X1 may be N.
Characteristics of the compound may be controlled or determined by introducing appropriate substituents to the core structure having excellent electron characteristics.
The compound for an organic optoelectronic device may have various energy band gaps by introducing the various other substituents to the core part and the substituent substituted in the core part. Accordingly, the compound may be applied to an electron injection layer (EIL) and/or electron transport layer and may also be applied to an emission layer.
By applying the compound having an appropriate energy level according to the substituent of the compound to the organic photoelectric device, electron transport properties may be enforced to provide excellent effects on the efficiency and the driving voltage. Electrochemical and thermal stability may also be excellent, thereby helping to improve life-span characteristics during driving an organic photoelectric device.
The electron characteristic refers to a characteristic in which an electron formed in the negative electrode is easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a LUMO level.
The hole characteristic refers to a characteristic in which a hole formed in the positive electrode is easily injected into the emission layer and transported in the emission layer due to conductive characteristic according to a HOMO level.
In Chemical Formula 2, Ar1 to Ar3 may each independently be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group.
In an implementation, the compound may have an asymmetric structure. The asymmetric structure may have bipolar characteristics and may be provided by appropriately combining the substituents. The asymmetric structure having bipolar characteristics may help improve the electron transport property, and may help improve the luminous efficiency and performance of device using the same.
In Chemical Formula 2, the substituted or unsubstituted C3 to C30 heteroaryl group may include, e.g., a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted oxatriazolyl group, a substituted or unsubstituted thiatriazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphpyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, or the like. A combination thereof may be also included.
In Chemical Formula 2, the substituted or unsubstituted C6 to C30 aryl group may include, e.g., a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triperylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, or the like. A combination thereof may be also included.
In an implementation, at least one of Ar1 or Ar2 may be a substituted or unsubstituted C3 to C30 heteroaryl group. In this case, the electron characteristic of the entire compound may be further enforced by the electron characteristics of the heteroaryl groups.
In an implementation, Ar1 may be a substituted or unsubstituted C3 to C30 heteroaryl group, and Ar2 and Ar3 may each independently be a substituted or unsubstituted C6 to C30 aryl group. Thus, the molecule polarity may be controlled to help improve electron injection and transport capability.
Ar2 may be a substituted or unsubstituted C3 to C30 heteroaryl group, and Ar1 and Ar3 may each independently be a substituted or unsubstituted C6 to C30 aryl group. By polarizing the molecular polarity when having the structure, electron injecting and transporting properties may be improved.
By appropriately combining the substituent, the compound may have excellent thermal stability and excellent resistance to oxidation.
L1 to L3 may each independently be, e.g., a substituted or unsubstituted ethenylene, a substituted or unsubstituted ethynylene, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted pyrimidinylene, a substituted or unsubstituted triazinylene, or the like.
For example, L1 to L3 may have a π-bond. Thus, a triplet energy bandgap may be increased by controlling a total π-conjugation length of the compound, so as to be very usefully applied to the emission layer of an organic photoelectric device as phosphorescent host. In an implementation, the linking groups L1 to L3 may be not present, e.g., m, n, and/or o may be 0.
In an implementation, R1 and R2 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof.
The entire compound may have a bulk structure by controlling the substituents, so the crystallinity may be decreased. When the crystallinity of the entire compound is decreased, the life-span of organic photoelectric device using the same may be prolonged.
In an implementation, the compound for an organic optoelectronic device may be represented by one of the following Chemical Formulae A1 to A189.





































































































































































































































In an implementation, the compound for an organic optoelectronic device may be represented by one of the following Chemical Formulae B1 to B 175.





























































































































































































































































In an implementation, the compound for an organic optoelectronic device may be represented by one of the following Chemical Formulae C1 to C 173.























































































































































































































































The compound for an organic optoelectronic device according to an embodiment may have a glass transition temperature of 150° C. or higher and a thermal decomposition temperature of 400° C. or higher, indicating improved thermal stability. Accordingly, the compound may be used to produce an organic optoelectronic device having a high efficiency.
The compound for an organic optoelectronic device according to an embodiment may play a role in emitting light or injecting and/or transporting electrons, and may also act as a light emitting host with an appropriate dopant. For example, the compound for an organic optoelectronic device may be used as a phosphorescent or fluorescent host material, a blue light emitting dopant material, or an electron transporting material.
The compound for an organic optoelectronic device according to an embodiment may be used for an organic thin layer. Thus, the compound may help improve the life-span characteristic, efficiency characteristic, electrochemical stability, and thermal stability of an organic photoelectric device, and may help decrease the driving voltage.
Another embodiment provides an organic optoelectronic device that includes the compound for an organic optoelectronic device. The organic optoelectronic device may include, e.g., an organic photoelectric device, an organic light emitting diode, an organic solar cell, an organic transistor, an organic photo conductor drum, an organic memory device, or the like. For example, the compound for an organic optoelectronic device according to an embodiment may be included in an electrode or an electrode buffer layer in the organic solar cell to help improve the quantum efficiency, or it may be used as an electrode material for a gate, a source-drain electrode, or the like in the organic transistor.
Hereinafter, an organic light emitting diode will be described in detail.
An organic light emitting diode including an anode, a cathode, and at least one organic thin layer between the anode and the cathode. The at least one organic thin layer may include the compound for an organic optoelectronic device according to an embodiment.
The organic thin layer that may include the compound for an organic optoelectronic device may include a layer selected from the group of an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking layer, and a combination thereof. The at least one layer may include the compound for an organic optoelectronic device according to an embodiment. For example, the compound for an organic optoelectronic device according to an embodiment may be included in an electron transport layer (ETL) or an electron injection layer (EIL). In an implementation, when the compound for an organic optoelectronic device is included in the emission layer, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, e.g., as a fluorescent blue dopant material.
FIGS. 1 to 5 illustrate cross-sectional views showing organic photoelectric devices including the compound for an organic optoelectronic device according to an embodiment.
Referring to FIGS. 1 to 5, organic photoelectric devices 100, 200, 300, 400, and 500 according to an embodiment may include at least one organic thin layer 105 interposed between an anode 120 and a cathode 110.
The anode 120 may include an anode material laving a large work function to facilitate hole injection into an organic thin layer. The anode material may include: a metal such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combined metal and oxide such as ZnO:Al or SnO2:Sb; or a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but is not limited thereto. In an implementation, the anode may include a transparent electrode including indium tin oxide (ITO).
The cathode 110 may include a cathode material having a small work function to facilitate electron injection into an organic thin layer. The cathode material may include: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or a multi-layered material such as LiF/Al, Liq/Al, LiO2/Al, LiF/Ca, LiF/Al, and BaF2/Ca, but is not limited thereto. The cathode may include a metal electrode including aluminum as a cathode.
Referring to FIG. 1, the organic photoelectric device 100 may include an organic thin layer 105 including only an emission layer 130.
Referring to FIG. 2, a double-layered organic photoelectric device 200 may include an organic thin layer 105 including an emission layer 230 (including an electron transport layer (ETL)) and a hole transport layer (HTL) 140. As shown in FIG. 2, the organic thin layer 105 may include a double layer of the emission layer 230 and hole transport layer (HTL) 140. The emission layer 130 may also function as an electron transport layer (ETL), and the hole transport layer (HTL) 140 layer may have an excellent binding property with a transparent electrode such as ITO and/or an excellent hole transporting property.
Referring to FIG. 3, a three-layered organic photoelectric device 300 may include an organic thin layer 105 including an electron transport layer (ETL) 150, an emission layer 130, and a hole transport layer (HTL) 140. The emission layer 130 may be independently installed, and layers having an excellent electron transporting property or an excellent hole transporting property may be separately stacked.
As shown in FIG. 4, a four-layered organic photoelectric device 400 may include an organic thin layer 105 including an electron injection layer (EIL) 160, an emission layer 130, a hole transport layer (HTL) 140, and a hole injection layer (HIL) 170 (for adherence with the anode of ITO).
As shown in FIG. 5, a five layered organic photoelectric device 500 may include an organic thin layer 105 including an electron transport layer (ETL) 150, an emission layer 130, a hole transport layer (HTL) 140, and a hole injection layer (HIL) 170, and may further include an electron injection layer (EIL) 160 to achieve a low voltage.
In FIGS. 1 to 5, the organic thin layer 105 including at least one selected from the group of an electron transport layer (ETL) 150, an electron injection layer (EIL) 160, emission layers 130 and 230, a hole transport layer (HTL) 140, a hole injection layer (HIL) 170, and combinations thereof may include a compound for an organic optoelectronic device. The compound for an organic optoelectronic device may be used for an electron transport layer (ETL) 150 including the electron transport layer (ETL) 150 or electron injection layer (EIL) 160. When it is used for the electron transport layer (ETL), it is possible to provide an organic photoelectric device having a simplified structure because an additional hole blocking layer (not shown) may be omitted.
Furthermore, when the compound for an organic optoelectronic device is included in the emission layers 130 and 230, the material for the organic photoelectric device may be included as a phosphorescent or fluorescent host or a fluorescent blue dopant.
The organic light emitting diode may be fabricated by: forming an anode on a substrate; forming an organic thin layer in accordance with a dry coating method such as evaporation, sputtering, plasma plating, and ion plating or a wet coating method such as spin coating, dipping, and flow coating; and providing a cathode thereon.
Another embodiment provides a display device including the organic photoelectric device according to the above embodiment.
The following Examples and Comparative Examples are provided in order to set forth particular details of one or more embodiments. However, it will be understood that the embodiments are not limited to the particular details described. Further, the Comparative Examples are set forth to highlight certain characteristics of certain embodiments, and are not to be construed as either limiting the scope of the invention as exemplified in the Examples or as necessarily being outside the scope of the invention in every respect.
(Preparation of Compound for an Organic Optoelectronic Device)
EXAMPLE 1
Synthesis of Compound Represented by Chemical Formula A1
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A1 was synthesized through 4 step processes in accordance with the following Reaction Scheme 1.







First Step: Synthesis of Intermediate Product (A)
25.0 g (112.6 mmol) of 1-amino-4-bromonaphthalene, 30.0 g (135.1 mmol) of 9-phenanthrene boronic acid, and 3.3 g (2.8 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 750 mL of a toluene solvent. A solution in which 31.1 g (225.1 mmol) of potassium carbonate (K2CO3) was dissolved in 250 ml of water was added thereto, and then reacted at 85° C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The obtained solid mixture was separated by a column and dried to provide a yellow solid of an intermediate product (A) in 31.0 g (yield: 86%).
Second Step: Synthesis of Intermediate Product (B)
20.0 g (62.6 mmol) of the intermediate product (A) and 9.8 g (93.9 mmol) of malonic acid were dissolved in a 58 mL of phosphorus oxychloride (POCl3) solvent and reacted at 140° C. for 4 hours. The obtained reaction products were poured into ice water and filtered. The formed solid was rinsed with water and a sodium hydrogen carbonate saturated aqueous solution. The obtained solid mixture was rinsed with methanol and dried to provide a pale yellow solid of an intermediate product (B) in 13.0 g (yield: 49%).
Third Step: Synthesis of Intermediate Product (C)
14.0 g (33.0 mmol) of intermediate product (B), 8.1 g (36.3 mmol) of 9-phenanthrene boronic acid, and 1.2 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 280 mL of a tetrahydrofuran (THF) solvent. A solution in which 9.1 g (66.0 mmol) of potassium carbonate (K2CO3) was dissolved in 140 ml of water was added thereto, and then they were reacted at 80° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of an intermediate compound (C) in 14.9 g (yield: 51%).
Fourth Step: Synthesis of Compound Represented by Chemical Formula A1
10.0 g (17.7 mmol) of intermediate product (C), 7.0 g (21.2 mmol) of 8-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinoline, and 0.6 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 200 mL of a tetrahydrofuran (THF) solvent. A solution in which 4.9 g (35.3 mmol) of potassium carbonate (K2CO3) was dissolved in 100 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 11.0 g (yield: 85%). (calculation value: 734.88, measurement value: MS[M+1] 735.18)
EXAMPLE 2
Synthesis of Compound Represented by Chemical Formula B1
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula B1 was synthesized through 2 step processes in accordance with the following Reaction Scheme 2.







First Step: Synthesis of Intermediate Product (D)
5.2 g (12.3 mmol) of the intermediate product (B), 4.5 g (13.5 mmol) of 8-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinoline, and 0.4 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in a 100 mL of a tetrahydrofuran (THF) solvent. A solution in which 3.4 g (24.5 mmol) of potassium carbonate (K2CO3) was dissolved in 50 ml of water was added thereto, and then they were reacted at 80° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of an intermediate product (C) in 5.0 g (yield: 69%).
Second Step: Synthesis of Compound Represented by Chemical Formula B1
5.0 g (8.4 mmol) of intermediate product (D), 2.3 g (10.1 mmol) of 9-phenanthrene boroic acid, and 0.3 g (0.3 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 100 mL of a tetrahydrofuran (THF) solvent. A solution in which 2.3 g (16.9 mmol) of potassium carbonate (K2CO3) was dissolved in 50 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 4.2 g (yield: 68%). (calculation value: 734.88, measurement value: MS[M+1] 735.18)
EXAMPLE 3
Synthesis of Compound Represented by Chemical Formula C1
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula C1 was synthesized through 3 step processes in accordance with the following Reaction Scheme 3.







First Step: Synthesis of Intermediate Product (E)
15.0 g (67.5 mmol) of 1-amino-4-bromonaphthalene, 24.6 g (74.3 mmol) of 8-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinoline, and 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 450 mL of a toluene solvent. A solution in which 18.7 g (135.1 mmol) of potassium carbonate (K2CO3) was dissolved in 150 ml of water was added thereto, and then they were reacted at 85° C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The obtained solid mixture was separated by a column and dried to provide a yellow solid of an intermediate product (E) in 15.5 g (yield: 66%).
Second Step: Synthesis of Intermediate Product (F)
15.5 g (44.7 mmol) of intermediate product (E), and 7.0 g (67.1 mmol) of malonic acid were dissolved in 41 mL of phosphorus oxychloride (POCl3) solvent and reacted at 140° C. for 4 hours. The obtained reactant was poured into ice water and filtered. The formed solid was rinsed with sodium hydrogen carbonate saturated aqueous solution. The obtained solid mixture was rinsed with methanol and dried to provide a pale yellow solid of an intermediate product (F) in 5.0 g (yield: 25%).
Third Step: Synthesis of Compound Represented by Chemical Formula C1
2.2 g (4.9 mmol) of intermediate product (F), 2.4 g (10.7 mmol) of 9-phenanthrene boronic acid, and 0.3 g (0.2 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 60 mL of a tetrahydrofuran (THF) solvent. A solution in which 2.7 g (19.5 mmol) of potassium carbonate (K2CO3) was dissolved in 20 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 2.8 g (yield: 78%). (calculation value: 734.88, measurement value: MS[M+1] 735.18)
EXAMPLE 4
Synthesis of Compound Represented by Chemical Formula A2
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A2 was synthesized in accordance with the following Reaction Scheme 4.




10 g (17.7 mmol) of intermediate product (C), 8.1 g (21.2 mmol) of 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phenantridine, and 0.6 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 200 mL of a tetrahydrofuran (THF) solvent. A solution in which 4.9 g (35.3 mmol) of potassium carbonate (K2CO3) was dissolved in 100 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 11.0 g (yield: 79%). (calculation value: 784.94, measurement value: MS[M+1] 785.29)
EXAMPLE 5
Synthesis of Compound Represented by Chemical Formula B2
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula B2 was synthesized in accordance with the following Reaction Scheme 5.







First Step: Synthesis of Intermediate Product (G)
11.0 g (25.9 mmol) of intermediate product (C), 10.9 g (28.5 mmol) of 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phenantridine, and 0.9 g (0.8 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 220 ml of a tetrahydrofuran (THF) solvent. A solution in which 7.2 g (51.9 mmol) of potassium carbonate (K2CO3) was added into 110 ml of water was added thereto, and then they were reacted at 80° C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a pale yellow solid of intermediate product (G) in 13.69 g (yield: 82%).
Second Step: Synthesis of Compound Represented by Chemical Formula B2
13.0 g (20.2 mmol) of intermediate product (G), 5.4 g (24.3 mmol) of 9-phenanthrene boronic acid, and 0.7 g (0.6 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved with a solvent of 390 mL of toluene and 260 mL of tetrahydrofuran (THF). A solution in which 5.6 g (40.4 mmol) of potassium carbonate (K2CO3) was dissolved in 20 mL of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 13.1 g (yield: 83%). (calculation value: 784.94, measurement value: MS[M+1] 785.29)
EXAMPLE 6
Synthesis of Compound Represented by Chemical Formula A3
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A3 was synthesized through one step process in accordance with the following Reaction Scheme 6.




16.0 g (28.3 mmol) of intermediate product (C), 4.2 g (33.9 mmol) of 4-pyridine boronic acid, and 1.0 g (0.9 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 320 mL of a tetrahydrofuran (THF) solvent. A solution in which 7.8 g (56.5 mmol) of potassium carbonate (K2CO3) was dissolved in 160 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 13.0 g (yield: 75%). (calculation value: 608.73, measurement value: MS[M+1] 609.23)
EXAMPLE 7
Synthesis of Compound Represented by Chemical Formula C2
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula C2 was synthesized through two step processes in accordance with the following Reaction Scheme 7.




First Step: Synthesis of Intermediate Product (H)
50.0 g (225.1 mmol) of 1-amino-4-bromonaphthalene, and 35.1 g (337.7 mmol) of malonic acid were dissolved in 345 ml of phosphorus oxychloride (POCl3) and reacted at 140° C. for 4 hours. The obtained reactant was poured into ice water and filtered. The formed solid was rinsed with sodium hydrogen carbonate saturated aqueous solution. The obtained solid mixture was rinsed with methanol and dried to provide a pale yellow solid of an intermediate product (H) in 16.6 g (yield: 23%).
Second Step: Synthesis of Compound Represented by Chemical Formula C2
8.0 g (24.5 mmol) of intermediate product (H), 19.6 g (88.1 mmol) of 9-phenanthrene boronic acid, and 2.1 g (1.8 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 240 mL of tetrahydrofuran (THF). A solution in which 20.3 g (146.8 mmol) of potassium carbonate (K2CO3) was dissolved in 120 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 12.0 g (yield: 69%). (calculation value: 707.86, measurement value: MS[M+1] 708.26)
EXAMPLE 8
Synthesis of compound Represented by Chemical Formula C3
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula C3 was synthesized through three step processes in accordance with the following Reaction Scheme 8.







First Step: Synthesis of Intermediate Product (I)
30.0 g (135.1 mmol) of 1-amino-4-bromonaphthalene, 41.8 g (148.6 mmol) of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 3.9 g (3.4 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 900 ml of a toluene solvent. A solution in which 37.3 g (270.2 mmol) of potassium carbonate (K2CO3) was dissolved in 300 ml of water was added thereto, and then they were reacted at 85° C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The obtained solid mixture was separated by a column and dried to provide a yellow solid of an intermediate product (I) in 24.9 g (yield: 62%).
Second Step: Synthesis of Intermediate Product (J)
24.9 g (84.1 mmol) of intermediate product (I), and 13.1 g (126.2 mmol) of malonic acid were dissolved in 38 mL of phosphorus oxychloride (POCl3) solvent and reacted at 140° C. for 4 hours. The obtained reactant was poured into ice water and filtered. The formed solid was rinsed with sodium hydrogen carbonate saturated aqueous solution. The obtained solid mixture was rinsed with methanol and dried to provide a pale yellow solid of an intermediate product (J) in 5.6 g (yield: 17%).
Third Step: Synthesis of Compound Represented by Chemical Formula C3
5.5 g (13.7 mmol) of intermediate product (J), 6.7 g (30.2 mmol) of 9-phenanthrene boronic acid, and 0.8 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 110 mL of a tetrahydrofuran (THF) solvent. A solution in which 7.6 g (54.8 mmol) of potassium carbonate (K2CO3) was dissolved in 55 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 6.0 g (yield: 64%). (calculation value: 684.82, measurement value: MS[M+1] 685.25)
EXAMPLE 9
Synthesis of Compound Represented by Chemical Formula A4
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A4 was synthesized in accordance with the following Reaction Scheme 9.




14.9 g (26.3 mmol) of intermediate product (C), 8.9 g (31.6 mmol) of 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 0.9 g (0.8 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 7.3 g (52.6 mmol) of potassium carbonate (K2CO3) was dissolved in 150 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 13.9 g (yield: 77%). (calculation value: 684.82, measurement value: MS[M+1] 685.25)
EXAMPLE 10
Synthesis of Compound Represented by Chemical Formula B3
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula B3 was synthesized through two step processes in accordance with the following Reaction Scheme 10.







First Step: Synthesis of Intermediate Product (K)
14.0 g (32.9 mmol) of intermediate product (C), 10.2 g (36.3 mmol) of 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 1.1 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 280 ml of a tetrahydrofuran (THF) solvent. http://www.splashdivecenter.com/ 9.1 g (66.0 mmol) of potassium carbonate (K2CO3) was dissolved in 140 ml of water was added thereto, and then they were reacted at 80° C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a pale yellow solid of intermediate product (K) in 9.7 g (yield: 54%).
Second Step: Synthesis of Compound Represented by Chemical Formula B3
9.7 g (17.8 mmol) of intermediate product (K), 5.4 g (21.4 mmol) of 9-phenanthrene boronic acid, and 0.6 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 380 mL of a tetrahydrofuran (THF) solvent. A solution in which 4.9 g (35.6 mmol) of potassium carbonate (K2CO3) was dissolved in 95 mL of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The residue was recrystallized with toluene, and the precipitated crystal was separated by a filter and rinsed with toluene and dried to provide a white solid of a compound in 10.0 g (yield: 82%). (calculation value: 684.82, measurement value: MS[M+1] 685.25)
EXAMPLE A-1
Synthesis of Compound Represented by Chemical Formula A27
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A27 was synthesized through 4 step processes in accordance with the following Reaction Scheme 11.







First Step: Synthesis of Intermediate Product (L)
100.0 g (450.3 mmol) of 1-amino-4-bromonaphthalene, 92.9 g (540.4 mmol) of 2-naphthaleneboronic acid, and 13.4 g (11.3 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 3000 ml of a toluene solvent. A solution in which 124.5 g (900.6 mmol) of potassium carbonate (K2CO3) was dissolved in 1,000 ml of water was added thereto, and then they were reacted at 100° C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The obtained solid mixture was rinsed with hexane two times to provide a yellow solid of intermediate product (L) in 105.5 g (yield: 87%).
Second Step: Synthesis of Intermediate Product (M)
105.5 g (391.7 mmol) of the intermediate product (L) and 61.1 g (587.6 mmol) of malonic acid were dissolved in a 358 mL of phosphorus oxychloride (POCl3) solvent and reacted at 140° C. for 4 hours. The obtained reactant was poured into ice water and filtered. The formed solid was rinsed with water and sodium hydrogen carbonate saturated aqueous solution. The obtained solid mixture was dissolved in 3,000 ml of toluene by filtering and concentrated using a rotary evaporator. 1,000 ml of hexane was added, followed by recrystallizing and drying to provide a pale yellow solid of an intermediate product (M) in 82.0 g (yield: 56%).
Third Step: Synthesis of Intermediate Product (N)
80.0 g (213.8 mmol) of the intermediate product (M), 36.8 g (213.8 mmol) of 2-naphthaleneboronic acid, and 7.4 g (6.4 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 1600 mL of a tetrahydrofuran (THF) solvent. A solution in which 59.1 g (427.5 mmol) of potassium carbonate (K2CO3) was dissolved in 800 ml of water was added thereto, and then they were reacted at 70° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with monochlorobenzene, precipitated crystals were separated by a filter, rinsed with monochlorobenzene, and dried to provide a white solid of an intermediate product (N) in 82.1 g (yield: 82%).
Fourth Step: Synthesis of Compound Represented by Chemical Formula A27
11.0 g (23.6 mmol) of the intermediate product (N), 9.4 g (28.3 mmol) of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinoline and 0.8 g (0.7 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in a 330 mL of a tetrahydrofuran (THF) solvent. A solution in which 6.5 g (47.2 mmol) of potassium carbonate (K2CO3) was dissolved in 110 ml of water was added thereto, and they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of the compound in 14.0 g (yield: 93%). (calculation value: 634.77, measurement value: MS[M+1] 635.08)
EXAMPLE A-2
Synthesis of Compound Represented by Chemical Formula A29
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A29 was synthesized in accordance with the following Reaction Scheme 12.




15.0 g (32.2 mmol) of the intermediate product (N), 10.9 g (38.6 mmol) of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 1.1 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 8.9 g (64.4 mmol) of potassium carbonate (K2CO3) was dissolved in 100 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 16.5 g (yield: 88%). (calculation value: 584.71, measurement value: MS[M+1] 585.01)
EXAMPLE A-3
Synthesis of Compound Represented by Chemical Formula A30
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A30 was synthesized in accordance with the following Reaction Scheme 13.




15.0 g (32.2 mmol) of the intermediate product (N), 10.9 g (38.6 mmol) of 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 1.1 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 8.9 g (64.4 mmol) of potassium carbonate (K2CO3) was dissolved in 100 ml of water was added thereto, and they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 17.2 g (yield: 91%). (calculation value: 584.71, measurement value: MS[M+1] 585.01)
EXAMPLE A-4
Synthesis of Compound Represented by Chemical Formula A31
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A31 was synthesized in accordance with the following Reaction Scheme 14.




15.0 g (32.2 mmol) of the intermediate product (N), 10.9 g (38.6 mmol) of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 1.1 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 8.9 g (64.4 mmol) of potassium carbonate (K2CO3) was dissolved in 100 ml of water was added thereto, and they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 17.0 g (yield: 90%). (calculation value: 584.71, measurement value: MS[M+1] 585.01)
EXAMPLE A-5
Synthesis of Compound Represented by Chemical Formula A33
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A33 was synthesized in accordance with the following Reaction Scheme 15.




16.0 g (34.3 mmol) of the intermediate product (N), 13.6 g (41.2 mmol) of 8-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinolinem, and 1.2 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 320 mL of a tetrahydrofuran (THF) solvent. A solution in which 9.5 g (68.7 mmol) of potassium carbonate (K2CO3) was dissolved in 180 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 20.0 g (yield: 83%). (calculation value: 634.77, measurement value: MS[M+1] 635.07)
EXAMPLE A-6
Synthesis of Compound Represented by Chemical Formula A43
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A43 was synthesized in accordance with the following Reaction Scheme 16.




16.0 g (34.3 mmol) of the intermediate product (N), 16.3 g (41.2 mmol) of 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzoimidazole, and 1.2 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 320 mL of a tetrahydrofuran (THF) solvent. A solution in which 9.5 g (68.7 mmol) of potassium carbonate (K2CO) was dissolved in 160 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 16.6 g (yield: 69%). (calculation value: 699.84, measurement value: MS[M+1] 700.14)
EXAMPLE A-7
Synthesis of Compound Represented by Chemical Formula A44
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A44 was synthesized in accordance with the following Reaction Scheme 17.




16.0 g (34.3 mmol) of the intermediate product (N), 16.3 g (41.2 mmol) of 2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzoimidazole, and 1.2 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 320 mL of a tetrahydrofuran (THF) solvent. A solution in which 9.5 g (68.7 mmol) of potassium carbonate (K2CO3) was dissolved in 160 ml of water was added thereto, and they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 23.0 g (yield: 96%). (calculation value: 699.84, measurement value: MS [M+1] 700.14)
EXAMPLE A-8
Synthesis of Compound Represented by Chemical Formula A142
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A142 was synthesized through 4 step processes in accordance with the following Reaction Scheme 18.







First Step: Synthesis of Intermediate Product (O)
100.0 g (450.3 mmol) of 1-amino-4-bromonaphthalene, 56.9 g (540.4 mmol) of phenylboroic acid, and 13.0 g (11.3 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 3,000 mL of a toluene solvent. A solution in which 124.5 g (900.6 mmol) of potassium carbonate (K2CO3) was dissolved in 1,000 ml of water was added thereto, and then they were reacted at 100° C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The obtained solid mixture was rinsed with hexane two times to provide a yellow solid of an intermediate product (O) in 72.0 g (yield: 73%).
Second Step: Synthesis of Intermediate Product (P)
72.0 g (328.4 mmol) of the intermediate product (O), and 51.3 g (492.4 mmol) of malonic acid were dissolved in 300 ml of phosphorus oxychloride (POCl3) and reacted at 140° C. for 4 hours. The obtained reactant was poured into ice water and filtered. The formed solid was rinsed with water and sodium hydrogen carbonate saturated aqueous solution. The obtained solid mixture was dissolved in 3,000 ml of toluene followed by filtering and then concentrated using a rotary evaporator. 1,000 ml of hexane was added, followed by recrystallizing and drying to provide a pale yellow solid of an intermediate product (P) in 56.6 g (yield: 53%).
Third Step: Synthesis of Intermediate Product (O)
55.0 g (169.7 mmol) of the intermediate product (P), 20.7 g (169.7 mmol) of phenylboroic acid, and 5.9 g (5.1 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 1,100 ml of a tetrahydrofuran (THF) solvent. A solution in which 46.9 g (339.3 mmol) of potassium carbonate (K2CO3) was dissolved in 550 ml of water was added thereto, and then they were reacted at 70° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The obtained solid mixture was rinsed with hexane two times to provide a yellow solid of an intermediate product (O) in 52.2 g (yield: 84%).
Fourth Step: Synthesis of Compound Represented by Chemical Formula A142
16.0 g (43.7 mmol) of the intermediate product (O), 20.8 g (52.5 mmol) of 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzoimidazole, and 1.5 g (1.3 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 320 ml of a tetrahydrofuran (THF) solvent. A solution in which 24.2 g (174.9 mmol) of potassium carbonate (K2CO3) was dissolved in 160 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 24.0 g (yield: 91%). (calculation value: 599.72, measurement value: MS[M+1] 600.02)
EXAMPLE A-9
Synthesis of Compound Represented by Chemical Formula A144
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A144 was synthesized in accordance with the following Reaction Scheme 19.




16.0 g (43.7 mmol) of the intermediate product (O), 20.8 g (52.5 mmol) of 2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzoimidazole, and 1.5 g (1.3 mmol) of tetrakis(triphenylphosphine)palladium[Pd(PPh3)4] were dissolved in 320 mL of a tetrahydrofuran (THF) solvent. A solution in which 24.2 g (174.9 mmol) of potassium carbonate (K2CO3) was dissolved in 160 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with monochlorobenzene, precipitated crystals were separated by a filter, rinsed with monochlorobenzene, and dried to provide a white solid of a compound in 21.7 g (yield: 83%). (calculation value: 599.72, measurement value: MS[M+1] 600.02)
EXAMPLE A-10
Synthesis of Compound Represented by Chemical Formula A156
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A156 was synthesized through 4 step processes in accordance with the following Reaction Scheme 20.







First Step: Synthesis of Intermediate Product (R)
100.0 g (450.3 mmol) of 1-amino-4-bromonaphthalene, 92.9 g (540.4 mmol) of 1-naphthaleneboroic acid, and 13.4 g (11.3 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 3,000 mL of a toluene solvent. A solution in which 124.5 g (900.6 mmol) of potassium carbonate (K2CO3) was dissolved in 1,000 ml of water was added thereto, and then they were reacted at 100° C. for 12 hours. The aqueous layer of the reaction was removed, the solvent was removed under reduced pressure, and the reaction product was rinsed with water and methanol. The obtained solid mixture was rinsed with hexane two times to provide a yellow solid of an intermediate product (L) in 100.0 g (yield: 82%).
Second Step: Synthesis of Intermediate Product (S)
102.0 g (378.7 mmol) of the intermediate product (R) and 59.1 g (568.1 mmol) of malonic acid were dissolved in 346 ml of phosphorus oxychloride (POCl3) and reacted at 140° C. for 4 hours. The obtained reactant was poured into ice water and filtered. The formed solid was rinsed with water and sodium hydrogen carbonate saturated aqueous solution. The obtained solid mixture was dissolved in 3,000 ml of toluene followed by filtering and then concentrated using a rotary evaporator. 1,000 ml of hexane was added followed by recrystallizing and drying to provide a pale yellow solid of an intermediate product (S) in 51.5 g (yield: 36%).
Third Step: Synthesis of Intermediate Product (T)
50.0 g (133.6 mmol) of the intermediate product (S), 23.0 g (133.6 mmol) of 1-naphthaleneboroic acid, and 4.6 g (4.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 1,000 ml of a tetrahydrofuran (THF) solvent. A solution in which 36.9 g (267.2 mmol) of potassium carbonate (K2CO3) was dissolved in 500 ml of water was added thereto, and then they were reacted at 70° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of an intermediate product (T) in 49.8 g (yield: 80%).
Fourth Step: Synthesis of Compound Represented by Chemical Formula A156
20.0 g (23.6 mmol) of the intermediate product (N), 18.1 g (64.4 mmol) of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine, and 1.5 g (1.3 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 400 ml of a tetrahydrofuran (THF) solvent. A solution in which 11.9 g (85.8 mmol) of potassium carbonate (K2CO3) was dissolved in 200 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 16.0 g (yield: 64%). (calculation value: 584.71, measurement value: MS[M+1] 585.01)
EXAMPLE A-11
Synthesis of Compound Represented by Chemical Formula A158
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A158 was synthesized in accordance with the following Reaction Scheme 21.




15.0 g (32.2 mmol) of the intermediate product (T), 8.9 g (48.3 mmol) of 8-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)quinoline, and 1.1 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 8.9 g (64.4 mmol) of potassium carbonate (K2CO3) was dissolved in 150 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 15.5 g (yield: 76%). (calculation value: 634.77, measurement value: MS[M+1] 635.07)
EXAMPLE A-12
Synthesis of Compound Represented by Chemical Formula A185
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A185 was synthesized in accordance with the following Reaction Scheme 22.




15.0 g (32.2 mmol) of the intermediate product (N), 8-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinoline 12.8 g (38.6 mmol) and tetrakis(triphenylphosphine)palladium[Pd PPh34] 1.9 g (1.6 mmol) were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 17.8 g (128.8 mmol) of potassium carbonate (K2CO3) was dissolved in 150 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 18.2 g (yield: 89%). (calculation value: 634.77, measurement value: MS[M+1] 635.07)
EXAMPLE A-13
Synthesis of Compound Represented by Chemical Formula A182
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A182 was synthesized in accordance with the following Reaction Scheme 23.




10.0 g (21.5 mmol) of the intermediate product (N), 8.6 g (25.8 mmol) of 8-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-yl)quinoline, and 1.2 g (1.1 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 200 ml of a tetrahydrofuran (THF) solvent. A solution in which 11.9 g (85.8 mmol) of potassium carbonate (K2CO3) was dissolved in 100 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 11.3 g (yield: 83%). (calculation value: 635.75, measurement value: MS[M+1] 636.05)
EXAMPLE A-14
Synthesis of Compound Represented by Chemical Formula A41
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A41 was synthesized in accordance with the following Reaction Scheme 24.




18.0 g (38.6 mmol) of the intermediate product (N), 14.9 g (46.4 mmol) of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)benzooxazole, and 1.3 g (1.2 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 360 ml of a tetrahydrofuran (THF) solvent. A solution in which 21.4 g (154.5 mmol) of potassium carbonate (K2CO3) was dissolved in 180 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 21.0 g (yield: 87%). (calculation value: 624.73, measurement value: MS[M+1] 625.03)
EXAMPLE A-15
Synthesis of Compound Represented by Chemical Formula A180
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A180 was synthesized in accordance with the following Reaction Scheme 25.




18.0 g (38.6 mmol) of the intermediate product (N), 13.1 g (46.4 mmol) of 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-yl)pyridine, and 1.3 g (1.2 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 360 ml of a tetrahydrofuran (THF) solvent. A solution in which 21.4 g (154.5 mmol) of potassium carbonate (K2CO3) was dissolved in 180 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 21.0 g (yield: 93%). (calculation value: 585.69, measurement value: MS[M+1] 585.99)
EXAMPLE A-16
Synthesis of Compound Represented by Chemical Formula A188
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A188 was synthesized through 2 step processes in accordance with the following Reaction Scheme 26.







First Step: Synthesis of Intermediate Product (U)
50.0 g (133.6 mmol) of the intermediate product (M), 29.7 g (133.6 mmol) of 9-phenanthreneboroic acid, and 4.6 g (4.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 1000 ml of a tetrahydrofuran (THF) solvent. A solution in which 36.9 g (267.2 mmol) of potassium carbonate (K2CO3) was dissolved in 500 ml of water was added thereto, and then they were reacted at 70° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with monochlorobenzene, precipitated crystals were separated by a filter, rinsed with monochlorobenzene, and dried to provide a white solid of an intermediate product (U) in 55.8 g (yield: 81%).
Second Step: Synthesis of Compound Represented by Chemical Formula A188
18.0 g (34.9 mmol) of the intermediate product (U), 16.6 g (41.9 mmol) of 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzoimidazole, and 1.2 g (1.1 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 360 ml of a tetrahydrofuran (THF) solvent. A solution in which 19.3 g (139.5 mmol) of potassium carbonate (K2CO3) was dissolved in 180 ml of water was added thereto, and then they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with monochlorobenzene, precipitated crystals were separated by a filter, rinsed with monochlorobenzene, and dried to provide a white solid of a compound in 21.0 g (yield: 80%). (calculation value: 749.90, measurement value: MS[M+1] 750.20)
EXAMPLE A-17
Synthesis of Compound Represented by Chemical Formula A189
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A189 was synthesized in accordance with the following Reaction Scheme 27.




18.0 g (34.9 mmol) of the intermediate product (U), 16.6 g (41.9 mmol) of 2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzoimidazole, and 1.2 g (1.1 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 320 mL of a tetrahydrofuran (THF) solvent. A solution in which 19.3 g (139.5 mmol) of potassium carbonate (K2CO3) was dissolved in 180 ml of water was added thereto, and they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 21.6 g (yield: 83%). (calculation value: 749.90, measurement value: MS[M+1] 750.20)
EXAMPLE A-18
Synthesis of Compound Represented by Chemical Formula A187
As an example of the compound for an organic optoelectronic device, the compound represented by the above Chemical Formula A187 was synthesized in accordance with the following Reaction Scheme 28.




18.0 g (34.9 mmol) of the intermediate product (U), 13.9 g (41.9 mmol) of 8-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-yl)quinoline, and 1.2 g (1.1 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in a 360 mL of a tetrahydrofuran (THF) solvent. A solution in which 19.3 g (139.5 mmol) of potassium carbonate (K2CO3) was dissolved in 180 ml of water was added thereto, and they were reacted at 90° C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 23.0 g (yield: 96%). (calculation value: 685.81, measurement value: MS[M+1] 686.11)
(Fabrication of Organic Light Emitting Diode)
EXAMPLE 11
As an anode, ITO having a thickness of 1,000 Å was used. As a cathode, aluminum (Al) having a thickness of 1,000 Å was used.
Specifically, organic light emitting diodes were fabricated as follows: an ITO glass substrate having sheet resistance of 15 Ω/cm2 was cut to a size of 50 mm×50 mm×0.7 mm and was ultrasonic wave cleaned in acetone, isopropylalcohol, and pure water for 5 minutes each, and UV ozone cleaned for 30 minutes to provide an anode.
N1,N1′-(biphenyl-4,4′-diyl)bis(N1-(naphthalen-2-yl)-N4,N4-diphenylbenzene-1,4-diamine) was deposited on the glass substrate to a thickness of 10 nm, and N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine was sequentially deposited to form a 40 nm-thick hole injection layer (HIL).
4 wt % of N,N,N′,N′-tetrakis(3,4-dimethylphenyechrysene-6,12-diamine and 96 wt % of 9-(3-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl)anthracene were deposited to provide a 25 nm-thick emission layer.
Subsequently, the compound synthesized in Example 1 was deposited to provide a 30 nm-thick electron transport layer (ETL).
Liq was vacuum-deposited on the electron transport layer (ETL) to provide a 0.5 nm-thick electron injection layer (EIL), and Al was vacuum-deposited to form a 100 nm-thick Liq/Al electrode.
EXAMPLE 12
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 3 was used for the electron transport layer (ETL), instead of using the compound synthesized from Example 1.
EXAMPLE 13
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 5 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE 14
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 7 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE 15
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 8 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE 16
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 9 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE 17
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 10 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE 18
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 1 and Liq at 1:1 (a ratio of weight) were deposited for the electron transport layer (ETL).
EXAMPLE 19
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 3 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE 20
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 5 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE 21
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 7 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE 22
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 8 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE 23
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 9 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE 24
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example 10 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE A-19
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-1 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-20
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-2 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-21
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-3 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-22
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-4 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-23
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-5 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-24
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-6 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-25
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-7 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-26
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-8 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-27
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-9 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-28
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-10 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-29
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-11 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-30
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-12 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-31
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-13 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-32
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-17 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
EXAMPLE A-33
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-1 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE A-34
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-3 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE A-35
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-6 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE A-36
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-7 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE A-37
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-9 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE A-38
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-10 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE A-39
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-12 and Liq at 1:1 were deposited for the electron transport layer (ETL).
EXAMPLE A-40
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound synthesized in Example A-17 and Liq at 1:1 were deposited for the electron transport layer (ETL).
COMPARATIVE EXAMPLE 1
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 11, except that the compound represented by the following Chemical Formula 3 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.




COMPARATIVE EXAMPLE 2
An organic light emitting diode was fabricated in accordance with the same procedure as in Example 18, except that the compound represented by the above Chemical Formula 3 was used for the electron transport layer (ETL) instead of using the compound synthesized from Example 1.
(Measurement of Performance of Organic Light Emitting Diode)
EXPERIMENTAL EXAMPLES
Each organic light emitting diode according to the Examples and Comparative Examples was measured for current density change depending upon the voltage, luminance change, and luminous efficiency. Specific measurement methods were as follows and the results are shown in the following Tables 1 and 2.
(1) Measurement of Current Density Change Depending on Voltage Change
The fabricated organic light emitting diodes were measured for current value flowing in the unit device while increasing the voltage from 0V to 10V using a current-voltage meter (Keithley 2400), and the measured current value was divided by area to provide the result.
(2) Measurement of Luminance Change Depending on Voltage Change
The fabricated organic light emitting diodes were measured for luminance while increasing the voltage from 0 V to 10 V using a luminance meter (Minolta Cs-1000A).
(3) Measurement of Luminous Efficiency
Current efficiency (cd/A) and electric power efficiency (lm/W) at the same luminance (1000 cd/m2) were calculated by using luminance and current density from the item (1) and (2) and voltage.









TABLE 1









Luminance at 500 cd/m2












Driving
Luminous
Electric power




voltage
efficiency
efficiency
CIE chromaticity













(V)
(cd/A)
(lm/W)
x
y
















Example 13
4.4
7.4
5.3
0.14
0.05


Example 15
3.9
5.4
4.3
0.14
0.05


Example 16
4.5
7.6
5.4
0.14
0.05


Example 17
4.2
6.2
4.6
0.14
0.05


Comparative
5.1
3.7
2.3
0.14
0.05


Example 1


Example 20
3.8
7.5
6.2
0.14
0.04


Example 23
3.8
8.2
6.9
0.14
0.05


Comparative
4.2
5.4
4.1
0.14
0.05


Example 2









As shown in Table 1, it may be seen that the organic light emitting diodes according to Examples 13, 15, 16, and 17 had lower driving voltages and improved luminous efficiency and electric power efficiency, compared with those of Comparative Example 1.
In addition, it may also be seen that the organic light emitting diodes according to Examples 20 and 23 had lower driving voltage and improved luminous efficiency and electric power efficiency, compared with those of Comparative Example 2.









TABLE 2









Luminance at 500 cd/m2












Driving
Luminous
Electric power




voltage
efficiency
efficiency
CIE chromaticity













(V)
(cd/A)
(lm/W)
x
y
















Example A-19
5.0
4.9
3.1
0.14
0.05


Example A-20
3.6
6.4
4.6
0.14
0.05


Example A-21
3.7
5.7
5.0
0.14
0.05


Example A-22
4.1
5.1
4.0
0.14
0.05


Example A-23
3.5
6.7
6.0
0.14
0.05


Example A-24
4.9
4.0
2.6
0.14
0.05


Example A-25
3.7
6.5
5.6
0.14
0.06


Example A-26
4.7
4.3
2.9
0.14
0.05


Example A-27
3.5
6.6
5.9
0.14
0.05


Example A-28
4.2
6.1
4.6
0.14
0.05


Example A-29
3.8
5.0
4.1
0.14
0.05


Example A-30
3.7
7.4
6.3
0.14
0.06


Example A-31
4.2
4.4
3.3
0.14
0.05


Example A-32
4.2
6.7
5.0
0.14
0.05


Comparative
5.1
3.7
2.3
0.14
0.05


Example 1


Example A-33
3.4
5.5
5.1
0.14
0.04


Example A-34
3.4
5.4
5.0
0.14
0.04


Example A-35
4.1
5.4
4.2
0.14
0.05


Example A-36
3.5
6.6
6.0
0.14
0.05


Example A-37
3.6
6.1
5.3
0.14
0.04


Example A-38
3.6
7.2
6.2
0.14
0.05


Example A-39
3.7
6.2
5.3
0.14
0.04


Example A-40
4.0
6.4
5.1
0.14
0.05


Comparative
4.2
5.4
4.1
0.14
0.05


Example 2









As shown in Table 2, it may be seen that the organic light emitting diodes according to Examples A-19 to A-40 had lower driving voltages and improved luminous efficiency and electric power efficiency, compared with those of Comparative Examples 1 and 2.
By way of summation and review, an organic light emitting diode may transform electrical energy into light by applying current to an organic light emitting material. The organic light emitting diode may have a structure in which a functional organic material layer is interposed between an anode and a cathode. The organic material layer may include a multi-layer including different materials, e.g., a hole injection layer (HIL), a hole transport layer (HTL), an emission layer, an electron transport layer (ETL), and/or an electron injection layer (EIL), in order to improve efficiency and stability of an organic photoelectric device.
In such an organic light emitting diode, when a voltage is applied between an anode and a cathode, holes from the anode and electrons from the cathode may be injected to an organic material layer and recombined to generate excitons having high energy. The generated excitons may generate light having certain wavelengths while shifting to a ground state.
A phosphorescent light emitting material may be used for a light emitting material of an organic light emitting diode, in addition to the fluorescent light emitting material. Such a phosphorescent material may emit lights by transiting the electrons from a ground state to an exited state, non-radiance transiting of a singlet exciton to a triplet exciton through intersystem crossing, and transiting a triplet exciton to a ground state to emit light.
As described above, in an organic light emitting diode, an organic material layer may include a light emitting material and a charge transport material, e.g., a hole injection material, a hole transport material, an electron transport material, an electron injection material, or the like.
The light emitting material may be classified as blue, green, and red light emitting materials (according to emitted colors), and yellow and orange light emitting materials to emit colors approaching natural colors.
When one material is used as a light emitting material, a maximum light emitting wavelength may be shifted to a long wavelength or color purity may decrease because of interactions between molecules, or device efficiency may decrease because of a light emitting quenching effect. Accordingly, a host/dopant system may be included as a light emitting material in order to help improve color purity and to help increase luminous efficiency and stability through energy transfer.
In order to achieve excellent performance of an organic light emitting diode, a material constituting an organic material layer, e.g., a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and/or a light emitting material such as a host and/or a dopant, should be stable and have good efficiency.
A low molecular weight organic light emitting diode may be manufactured as a thin film in a vacuum deposition method, and may have good efficiency and life-span performance. A polymer organic light emitting diode may be manufactured in an Inkjet or spin coating method and may have an advantage of low initial cost and being large-sized.
Both low molecular weight organic light emitting and polymer organic light emitting diodes have advantages of being self-light emitting and being ultrathin, and having a high speed response, a wide viewing angle, high image quality, durability, a large driving temperature range, and the like, and therefore it is highlighted as the next generation display. In particular, they have good visibility due to the self-light emitting characteristic (compared with a conventional LCD (liquid crystal display)) and have an advantage of decreasing thickness and weight of LCD by up to a third, because a backlight may be omitted.
In addition, low molecular weight organic light emitting and polymer organic light emitting diodes may have a response speed that is 1,000 times faster per microsecond unit than an LCD. Thus, a perfect motion picture may be realized without an after-image. Therefore, recently it may be as an optimal display in compliance with multimedia generation. Based on these advantages, low molecular weight organic light emitting and polymer organic light emitting diodes have been remarkably developed to have 80 times the efficiency and more than 100 times the life-span. Recently, these diodes have been used in displays that are rapidly becoming larger, such as for a 40-inch organic light emitting diode panel.
These displays may simultaneously have improved luminous efficiency and life-span in order to be larger. In order to increase the luminous efficiency, smooth combination between holes and electrons in an emission layer is desirable. However, an organic material may have slower electron mobility than hole mobility. Thus, electron injection from a cathode and mobility using efficient electron transport layer (ETL) should be heightened and transfer of a hole is should be inhibited, in order to realize efficient recombination of a hole and an electron in an emission layer. In addition, the device may have a decreased life-span if the material therein may be crystallized due to Joule heat generated when it is driven.
The embodiments provide an organic compound having excellent electron injection and mobility and high thermal stability.
The embodiments provide a compound for an organic optoelectronic device that may act as a light emitting, material, an electron injection and/or electron transporting material, or a light emitting host (along with an appropriate dopant).
The embodiments provide an organic light emitting diode having excellent life-span, efficiency, a driving voltage, electrochemical stability, and thermal stability.
The embodiments provide an organic optoelectronic device having excellent electrochemical and thermal stability and life-span characteristics, and high luminous efficiency at a low driving voltage.
Example embodiments have been disclosed herein, and although specific terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent to one of ordinary skill in the art as of the filing of the present application, features, characteristics, and/or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of skill in the art that various changes in form and details may be made without departing from the spirit and scope of the present invention as set forth in the following claims.

## Claims

1. A compound for an organic optoelectronic device, wherein the compound is represented by the following Chemical Formula 2:



wherein, in Chemical Formula 2:
X1 is —N,
R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
Ar1 to Ar3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group,
L1 to L3 are each independently a single bond, a substituted or unsubstituted C2 to C6 alkenyl group, a substituted or unsubstituted C2 to C6 alkynyl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof, and
n, m, and o are each 1.

2. The compound for an organic optoelectronic device as claimed in claim 1, wherein at least one of Ar1 or Ar2 is a substituted or unsubstituted C3 to C30 heteroaryl group.

3. The compound for an organic optoelectronic device as claimed in claim 1, wherein:
Ar1 is a substituted or unsubstituted C3 to C30 heteroaryl group, and
Ar2 and Ar3 are each independently a substituted or unsubstituted C6 to C30 aryl group.

4. The compound for an organic optoelectronic device as claimed in claim 1, wherein:
Ar2 is a substituted or unsubstituted C3 to C30 heteroaryl group, and
Ar1 and Ar3 are each independently a substituted or unsubstituted C6 to C30 aryl group.

5. The compound for an organic optoelectronic device as claimed in claim 1, wherein the substituted or unsubstituted C3 to C30 heteroaryl group is a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted oxatriazolyl group, a substituted or unsubstituted thiatriazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphpyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, or a combination thereof.

6. The compound for an organic optoelectronic device as claimed in claim 1, wherein the substituted or unsubstituted C6 to C30 aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triperylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, or a combination thereof.

7. The compound for an organic optoelectronic device as claimed in claim 2, wherein the organic optoelectronic device is selected from the group of an organic photoelectric device, an organic light emitting diode, an organic solar cell, an organic transistor, an organic photo conductor drum, and an organic memory device.

8. A compound for an organic optoelectronic device, the compound being represented by one of the following Chemical Formulae A1 to A189:

9. The compound for an organic optoelectronic device as claimed in claim 1, wherein the compound represented by Chemical Formula 2 is represented by one of the following Chemical Formulae B1 to B175 :

10. The compound for an organic optoelectronic device as claimed in claim 1, wherein the compound represented by Chemical Formula 2 is represented by one of the following Chemical Formulae C1 to C173:

11. An organic light emitting diode, comprising
an anode, a cathode, and at least one thin layer between the anode and the cathode,
wherein the at least one organic thin layer includes the compound for an organic optoelectronic device as claimed in claim 2.

12. The organic light emitting diode as claimed in claim 11, wherein the at least one organic thin layer is selected from the group of an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking layer, and a combination thereof.

13. The organic light emitting diode as claimed in claim 11, wherein the at least one organic thin layer includes an electron transport layer (ETL) or an electron injection layer (EIL), and the compound for an organic optoelectronic device is included in the electron transport layer (ETL) or the electron injection layer (EIL).

14. The organic light emitting diode as claimed in claim 11, wherein the at least one organic thin layer includes an emission layer, and the compound for an organic optoelectronic device is included in the emission layer.

15. The organic light emitting diode as claimed in claim 11, wherein the at least one organic thin layer includes an emission layer, and the compound for an organic optoelectronic device is a phosphorescent or fluorescent host material in the emission layer.

16. The organic light emitting diode as claimed in claim 11, wherein the at least one organic thin layer includes an emission layer, and the compound for an organic optoelectronic device is a fluorescent blue dopant material in the emission layer.

17. A display device including the organic light emitting diode as claimed in claim 11.

18. A compound for an organic optoelectronic device, the compound being represented by the following Chemical Formula 1:



wherein, in Chemical Formula 1:
X1 and X2 are each independently —N— or —CR'—, in which R′ is hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof, or forms a sigma bond with one of the *,
R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
Ar1 to Ar3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heteroaryl group, provided that at least one of Ar1 or Ar2 is a substituted or unsubstituted C3 to C30 heteroaryl group,
L1 to L3 are each independently a single bond, a substituted or unsubstituted C2 to C6 alkenyl group, a substituted or unsubstituted C2 to C6 alkynyl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof, and
n, m, and o are each 1.

19. A compound for an organic optoelectronic device, the compound being represented by the following Chemical Formula 1:



wherein, in Chemical Formula 1:
X1 and X2 are each independently —N— or —CR′—, in which R′ is hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof, or forms a sigma bond with one of the *,
R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
Ar1 is a substituted or unsubstituted C3 to C30 heteroaryl group,
Ar2 and Ar3 are each independently a substituted or unsubstituted C6 to C30 aryl group,
L1 to L3 are each independently a single bond, a substituted or unsubstituted C2 to C6 alkenyl group, a substituted or unsubstituted C2 to C6 alkynyl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof, and n, m, and o are each 1.