Abstract
`Disclosed are a compound including a 5-membered heterocycle,
`an organic electric element comprising the same, and a terminal
`thereof.
`
`[Figure accompanying the abstract]
`FIG.1
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000001
`
`
`Disclosed are a compound including a 5-membered heterocycle,
`an organic electric element comprising the same, and a terminal
`thereof.
`
`[Figure accompanying the abstract]
`FIG.1
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000001
`
`
`
`COMPOUND CONTAINING 5-MEMBERED HETEROCYCLE, ORGANIC ELECTRIC
`ELEMENT COMPRISING THE SAME AND TERMINAL THEREOF
`
`BACKGROUND
`Technical Field
`The present invention relates to compounds including 5-
`membered heterocycle, organic electric elements comprising the
`same, and terminals thereof.
`
`Background Art
`In general, an organic light emitting phenomenon indicates
`conversion of electric energy into light energy by means of an
`organic material. An organic electronic device using the organic
`light emitting phenomenon generally has a structure including an
`anode, a cathode, and an organic material layer interposed
`therebetween. Herein, in many cases, the organic material layer
`may have a multi-layered structure having respectively different
`materials in order to improve efficiency and stability of an
`organic electronic device. For example, it may include a hole
`injection layer, a hole transport layer, a light emitting layer,
`an electron transport layer, an electron injection layer, or the
`like.
`Materials used as an organic material layer in an organic
`electronic
`device
`may be classified into a
`light emitting
`material and a charge transport material, for example, a hole
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000002
`
`
`
`material, an electron
`a hole transport
`injection material,
`an
`electron
`injection
`material,
`etc.
`transport
`material,
`according to their functions. Then, the light emitting material
`may be divided into a high molecular weight type and a low
`molecular weight type according to their molecular weight, and
`may be divided into a fluorescent material from electronic
`singlet
`excited
`states
`and
`a
`phosphorescent
`material
`from
`electronic
`triplet excited
`states
`according to their
`light
`emitting mechanism. Further, the light emitting material can be
`classified into a blue, green or red light emitting material and
`a yellow or orange light emitting material required for giving a
`more natural color, according to a light emitting color.
`Meanwhile, when only one material is used as a light
`emitting material, an efficiency of a device is lowered owing to
`a maximum
`luminescence
`wavelength
`being moved
`to
`a longer
`wavelength due to the interaction between the molecules, the
`deterioration
`of
`color
`purity
`and
`the
`reduction
`in
`light
`emitting efficiency. Therefore, a host/dopant system can be used
`as the light emitting material for the purpose of enhancing the
`color purity and the light emitting efficiency through energy
`transfer. It is based on the principle that if a small amount of
`a dopant having a smaller energy band gap than a host forming a
`light emitting layer is mixed with the light emitting layer,
`excitons which are generated in the light emitting layer are
`transported to the dopant, thus emitting a light having a high
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000003
`
`
`
`efficiency. Here, since the wavelength of the host is moved
`according to the wavelength of the dopant, a light having a
`desired wavelength can be obtained according the kind of the
`dopant.
`In order to allow the organic electronic device to fully
`exhibit
`the
`above-mentioned
`excellent
`characteristics,
`a
`material constituting the organic material layer in the device,
`for
`example,
`a
`hole
`injection
`material,
`a
`hole
`transport
`material, a
`light emitting material,
`an
`electron
`transport
`material,
`an
`electron
`injection
`material,
`etc.
`should
`be
`essentially composed of a stable and efficient material. However,
`the development of a stable and efficient organic material layer
`material for the organic electronic device has not yet been
`fully realized. Accordingly, the development of new materials is
`continuously desired.
`
`DETAILED DESCRIPTION OF THE INVENTION
`Technical Problem
`The present inventors have found out a compound including
`two or more 5-membered heterocycles having a new structure. In
`addition, the inventors have found out the fact that when an
`organic material layer of an organic electric element is formed
`by using the new compound, effects such as an increase in
`efficiency, stability and lifetime can be obtained.
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000004
`
`
`
`An object of the present invention is to provide a novel
`compound including 5-membered heterocycle, an organic electric
`element comprising the same, and a terminal thereof.
`
`Technical Solution
`In accordance with an aspect of the present invention,
`there is provided a compound represented by Formula below.
`
`The inventive compound including two or more 5-membered
`heterocycles may be used as a hole injection material, a hole
`transport
`material,
`a
`light
`emitting
`material,
`and/or
`an
`electron transport material appropriate for a fluorescent or
`phosphorescent device of all colors such as red, green, blue,
`white, etc., and is useful as a host material for various colors
`of a phosphorescent dopant.
`In another aspect of the present invention, there are
`provided
`an
`organic
`electric
`element
`using
`the
`compound
`represented by Formula
`above and
`a terminal including
`the
`organic electric element.
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000005
`
`
`
`Advantageous Effects
`The compound including two or more 5-membered heterocycles
`may be used various role in n organic electric element and a
`terminal. And
`the compound is useful as a
`hole
`injection
`material, a hole transport material, a light emitting material,
`and/or
`an
`electron
`transport
`material
`appropriate
`for
`a
`fluorescent or phosphorescent device of all colors such as red,
`green, blue, white, etc., and is useful as a host material for
`various colors of a phosphorescent dopant.
`
`DETAILED DESCRIPTION
`Hereinafter, some embodiments of the present invention will
`described in detail with reference
`to
`the accompanying
`be
`illustrative drawings.
`In designation of reference numerals to components in
`respective drawings, it should be noted that the same elements
`will be designated by the same reference numerals although they
`are shown in different drawings. Further, in the following
`description of the present invention, a detailed description of
`known functions and configurations incorporated herein will be
`omitted when it may make the subject matter of the present
`invention rather unclear.
`In addition, terms, such as first, second, A, B, (a), (b)
`or the like may be used herein when describing components of the
`present invention. Each of these terminologies is not used to
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000006
`
`
`
`corresponding
`a
`of
`sequence
`or
`order
`essence,
`an
`define
`corresponding
`distinguish the
`to
`merely
`component but
`used
`component from other component(s). It should be noted that if it
`is
`described
`in
`the
`specification
`that
`one
`component
`is
`“connected,” “coupled” or “joined” to another component, a third
`component may be “connected,” “coupled,” and “joined” between
`the first and second components, although the first component
`may be directly connected, coupled or joined to the second
`component.
`In accordance with an aspect of the present invention,
`there is provided a compound represented by Formula 1 below.
`[Formula 1]
`
`Wherein,
`(1) R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 are
`each independently a hydrogen atom, a halogen atom, a cyano
`group,
`an
`alkoxy
`group,
`a
`thiol
`group,
`a
`substituted
`or
`unsubstituted alkyl
`group having 1 to 50 carbon atoms, a
`substituted or unsubstituted alkoxy group having 1 to 50 carbon
`atoms, a substituted or unsubstituted alkenyl group having 1 to
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000007
`
`
`
`50 carbon atoms, a substituted or unsubstituted arylene group
`having 5 to 60 carbon atoms, a substituted or unsubstituted aryl
`group
`having
`5
`to
`60
`carbon
`atoms,
`a
`substituted
`or
`unsubstituted aryloxy group having 5 to 60 carbon atoms, a
`substituted or unsubstituted alkyl
`group having 1 to 50 carbon
`atoms and containing at least one heteroatom selected from the
`group
`consisting
`of
`sulfur
`(S),
`nitrogen
`(N),
`oxygen(O),
`phosphorous (P) and silicon (Si), a substituted or unsubstituted
`heteroaryl group having 5 to 60 carbon atoms and containing at
`least one heteroatom selected from the group consisting of
`sulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon
`(Si), or a substituted or unsubstituted heteroaryloxy group
`having
`5 to 60 carbon atoms
`and containing at least
`one
`heteroatom selected from the group consisting of sulfur (S),
`nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si),
`(2) R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, R7
`and R8, R9 and R10, R10 and R11, and R11 and R12 are each able to
`form a saturated or unsaturated ring together with an adjacent
`group,
`(3) X is at least one selected from the group consisting of
`sulfur(S), oxygen(O) and silicon(Si),
`(4) Y is a hydrogen atom, a halogen atom, a cyano group, an
`alkoxy group, a thiol group, a substituted or unsubstituted
`alkyl
`group having 1 to 50 carbon atoms, a substituted or
`unsubstituted alkenyl group having 1 to 50 carbon atoms, a
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000008
`
`
`
`substituted or unsubstituted arylene group having 5 to 60 carbon
`atoms, a substituted or unsubstituted aryl group having 5 to 60
`carbon
`atoms,
`a substituted
`or
`unsubstituted aryloxy
`group
`having 5 to 60 carbon atoms, a substituted or unsubstituted
`alkyl group having 1 to 50 carbon atoms and containing at least
`one heteroatom selected from the group consisting of sulfur (S),
`nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), a
`substituted or unsubstituted heteroaryl group having 5 to 60
`carbon atoms and containing at least one heteroatom selected
`from the group consisting of sulfur (S), nitrogen (N), oxygen(O),
`phosphorous
`(P)
`and
`silicon
`(Si),
`or
`a
`substituted
`or
`unsubstituted heteroaryloxy group having 5 to 60 carbon atoms
`and containing at least one heteroatom selected from the group
`consisting of sulfur (S), nitrogen (N), oxygen(O), phosphorous
`(P) and silicon (Si),
`(5) n is an integer from 1 to 3, and
`(6) the compound having Formula 1 may be used for a soluble
`process.
`In accordance with another aspect of the present invention,
`there is provided a compound represented by Formula 2 below.
`[Formula 2]
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000009
`
`
`
`In accordance with another aspect of the present invention,
`there is provided a compound represented by Formula 3 below.
`[Formula 3]
`
`In Formula 2 and 3, X and Y may be equally defined as in
`Formula 1.
`In accordance with another aspect of the present invention,
`there is provided a compound represented by Formula 4 below.
`[Formula 4]
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000010
`
`
`
`Wherein,
`(7) R13 is a hydrogen atom, a halogen atom, a substituted or
`unsubstituted alkyl
`group having 1 to 50 carbon atoms, a
`substituted or unsubstituted alkenyl group having 1 to 50 carbon
`atoms, a substituted or unsubstituted arylene group having 5 to
`60 carbon atoms, a substituted or unsubstituted aryl group
`having 5 to 60 carbon atoms, or a substituted or unsubstituted
`heteroaryl group having 5 to 60 carbon atoms and containing at
`least one heteroatom selected from the group consisting of
`sulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon
`(Si), and
`(8) Ar1 and Ar2 is each independently a hydrogen atom, a
`halogen atom, a substituted or unsubstituted alkyl group having
`1 to 50 carbon atoms, a substituted or unsubstituted alkenyl
`group
`having
`1
`to
`50
`carbon
`atoms,
`a
`substituted
`or
`unsubstituted arylene group having 5 to 60 carbon atoms, a
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000011
`
`
`
`substituted or unsubstituted aryl group having 5 to 60 carbon
`atoms, or a substituted or unsubstituted heteroaryl group having
`5 to 60 carbon atoms and containing at least one heteroatom
`selected from the group consisting of sulfur (S), nitrogen (N),
`oxygen(O), phosphorous (P) and silicon (Si).
`In accordance with another aspect of the present invention,
`there is provided a compound represented by Formula 5 below.
`[Formula 5]
`
`Wherein,
`(9) R14 and R15 are each independently a hydrogen atom, a
`halogen atom, a substituted or unsubstituted alkyl group having
`1 to 50 carbon atoms, a substituted or unsubstituted alkenyl
`group
`having
`1
`to
`50
`carbon
`atoms,
`a
`substituted
`or
`unsubstituted arylene group having 5 to 60 carbon atoms, a
`substituted or unsubstituted aryl group having 5 to 60 carbon
`atoms, or a substituted or unsubstituted heteroaryl group having
`5 to 60 carbon atoms and containing at least one heteroatom
`selected from the group consisting of sulfur (S), nitrogen (N),
`oxygen(O), phosphorous (P) and silicon (Si), and
`(10) Z is independently a single bond, -O-, -S-, -CO-, -
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000012
`
`
`
`SO2-, -NR16-, -PR17-, -SiR18R19-, a substituted or unsubstituted
`alkyl
`group having 1 to 50 carbon atoms, a substituted or
`unsubstituted alkenyl group having 1 to 50 carbon atoms, a
`substituted or unsubstituted arylene group having 5 to 60 carbon
`atoms, a substituted or unsubstituted aryl group having 5 to 60
`carbon atoms, or a substituted or unsubstituted heteroaryl group
`having
`5 to 60 carbon atoms
`and containing at least
`one
`heteroatom selected from the group consisting of sulfur (S),
`nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si).
`The compound represented by Formulas 2 to 5 may be used for
`a soluble process.
`According to one embodiment of the present invention,
`specific examples of the compound including two or more 5-
`membered heterocycles, represented by Formulas 1 to 5, may
`include compounds represented by Formula 6. However, the present
`invention is not limited thereto.
`[Formula 6]
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000013
`
`
`
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`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000014
`
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`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000015
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000015
`
`
`
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`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000016
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000016
`
`
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`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000017
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000017
`
`
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`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000018
`
`
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000019
`
`
`
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000020
`
`
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000021
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000021
`
`
`
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`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000022
`
`
`
`
`
`xriél S 125
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`flE§1%
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`fl§E1H
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000023
`
`
`
`
`
`There exist various organic electric devices which employ
`compounds including two or more 5-membered heterocycles, as
`described with reference to Formulas 1 to 6, as an organic
`material layer. The organic electric devices in which compounds
`including two or more 5-membered heterocycles, as described with
`reference to Formulas 1 to 6, can be employed, may include, for
`example, an organic light emitting diode (OLED), an organic
`solar
`cell,
`an
`organic
`photo
`conductor
`(OPC),
`an
`organic
`transistor (organic TFT), a photodiode, an organic laser, and a
`laser diode, or the like.
`As one example of the organic electric devices in which
`compounds including two or more 5-membered heterocycles, as
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000024
`
`
`
`described with reference to Formulas 1 to 6, can be used, an
`organic light emitting diode (OLED) will be described below, but
`the
`present
`invention
`is
`not
`limited
`thereto.
`The
`above
`described compound including two or more 5-membered heterocycles
`may be applied to various organic electric devices.
`In another embodiment of the present invention, there is
`provided an OLED including a first electrode, a second electrode,
`and
`an
`organic
`material
`layer
`interposed
`between
`these
`electrodes, in which at least one of organic material layers
`includes the compounds represented by Formulas 1 to 6.
`FIGs. 1 to 6 illustrate examples of an OLED which can
`employ a compound according to an embodiment of the present
`invention.
`The OLED according to another embodiment of the present
`invention may be manufactured by means of a manufacturing method
`and materials conventionally known in the art in such a manner
`that it can have a conventionally known structure, except that
`at
`least one
`of
`organic material layers including
`a hole
`injection layer, a hole transport layer, a light emitting layer,
`an electron transport layer, and an electron injection layer is
`formed in such a manner that it can include the compounds
`represented by Formulas 1 to 6.
`The structures of the OLED according to another embodiment
`of the present invention are shown in FIGs. 1 to 6, but the
`present invention is not limited to the structures. Herein, the
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000025
`
`
`
`reference numeral 101 indicates a substrate, 102 indicates an
`anode, 103 indicates a hole injection layer (HIL), 104 indicates
`a hole transport layer (HTL), 105 indicates a light emitting
`layer (EML), 106 indicates an electron injection layer (EIL),
`107
`indicates
`an
`electron
`transport
`layer
`(ETL),
`and
`108
`indicates a cathode. Although not shown, such an OLED may
`further
`include
`a
`hole
`blocking
`layer
`(HBL)
`for
`blocking
`movement of holes, an electron blocking layer (EBL) for blocking
`movement of electrons, and a protective layer. The protective
`layer may be formed in such a manner that it, as an uppermost
`layer, can protect an organic material layer or a cathode.
`Herein, the compound including two or more 5-membered
`heterocycles, as described with reference to Formulas 1 to 12,
`may be included in at least one of organic material layers
`including a hole injection layer, a hole transport layer, a
`light
`emitting
`layer,
`and
`an
`electron
`transport
`layer.
`Specifically, the compound including two or more 5-membered
`heterocycles, as described with reference to Formulas 1 to 12,
`may be substituted for at least one of a hole injection layer, a
`hole
`transport layer, a
`light emitting layer, an electron
`transport layer, an electron injection layer, a hole blocking
`layer, an electron blocking layer, and a protective layer, or
`may be used in combination with these layers. Of course, the
`compound may be used for not only one layer of the organic
`material layers but also two or more layers.
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000026
`
`
`
`The compound including two or more 5-membered heterocycles,
`as described with reference to Formulas 1 to 6,
`may be used
`various role in n organic electric element and a terminal. And
`the compound is useful as a hole injection material, a hole
`transport
`material,
`a
`light
`emitting
`material,
`and/or
`an
`electron transport material appropriate for a fluorescent or
`phosphorescent device of all colors such as red, green, blue,
`white, etc., and is useful as a host material for various colors
`of a phosphorescent dopant.
`For example, in manufacturing of the OLED according to
`another
`embodiment
`of
`the
`present
`invention,
`a
`metal,
`a
`conductive metal oxide, or an alloy thereof is deposited on a
`substrate by means of PVD (physical vapor deposition) such as
`sputtering or e-beam evaporation so as to form an anode, and
`then an organic material layer including a hole injection layer,
`a hole transport layer, a light emitting layer, an electron
`transport layer, and an electron injection layer is formed
`thereon, and a material used as a cathode is deposited thereon.
`Besides, on a substrate, a cathode material, an organic
`material
`layer,
`and an anode
`material
`may be sequentially
`deposited so as to provide an organic electronic device. The
`organic
`material
`layer
`may
`be
`formed
`in
`a
`multi-layered
`structure including a hole injection layer, a hole transport
`layer, a light emitting layer, an electron transport layer, and
`an electron injection layer, but the present invention is not
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000027
`
`
`
`limited thereto. It may be formed in a single layer structure.
`Further, the organic material layer may be manufactured with a
`smaller number of layers by using various polymer materials by
`means of a solvent process e.g., spin coating, dip coating,
`doctor blading, screen printing, inkjet printing, or thermal
`transfer, instead of deposition.
`In the OLED according to another embodiment of the present
`invention, the organic material layer, such as a light emitting
`layer, may be formed by a soluble process of the above described
`compound including two or more 5-membered heterocycles.
`The substrate is a support for the OLED, and may employ a
`silicon wafer, a quartz or glass plate, a metallic plate, a
`plastic film or sheet.
`On the substrate, an anode is positioned. Such an anode
`allows
`holes
`to
`be
`injected
`into
`a
`hole
`injection
`layer
`positioned thereon. As an anode material, a material having a
`high work function is preferably used so that injection of holes
`into an organic material layer can be smoothly carried out.
`Specific examples of an anode material used for the present
`invention may include: metals such as vanadium, chromium, copper,
`zinc, gold, or alloys thereof; metallic oxides such as zinc
`oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide
`(IZO); a metal-oxide combination such as ZnO:Al or SnO2:Sb; and
`conductive polymers such as poly(3-methylthiophene), poly[3,4-
`(ethylene-1,2-dioxy)thiophene](PEDT),
`polypyrrole
`and
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000028
`
`
`
`polyaniline, but the present invention is not limited thereto.
`On the anode, a hole injection layer is positioned. A
`material for such a hole injection layer is required to have a
`high efficiency for injecting holes from an anode, and to be
`able to efficiently transport the injected holes. For this, the
`material has a low ionization potential, a high transparency
`against visible light, and a high stability for holes.
`As a hole injection material, a material into which holes
`can be well injected from an anode at a low voltage is used.
`Preferably, HOMO (highest occupied molecular orbital) of the
`hole injection material ranges from a work function of an anode
`material to HOMO of adjacent organic material layers. Specific
`examples
`of
`the hole injection
`material
`may include
`metal
`porphyrine-,
`oligothiophene-,
`and
`arylamine-based
`organic
`materials,
`hexanitrile
`hexaazatriphenylen-
`and
`quinacridone-
`based organic materials, perylene-based organic materials, and
`anthraquinone-, polyaniline-, and polythiophene-based conductive
`polymers, but the present invention is not limited thereto.
`On the hole injection layer, a hole transport layer is
`positioned.
`Such
`a
`hole
`transport
`layer
`receives
`holes
`transferred from the hole injection layer and transfers them to
`an organic luminescence layer positioned thereon. Further, the
`hole transport layer has a high hole mobility and a high hole
`stability and performs a role of blocking electrons. Besides
`these general requirements, it requires heat-resistance against
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000029
`
`
`
`a device when applied for car display, and thus is preferably
`made of a material having a glass transition temperature (Tg) of
`70℃ or more. The examples of a material satisfying these
`conditions
`may
`include
`NPD
`(or
`NPB),
`spiro-arylamine-based
`compound, perylene-arylamine-based compound, azacycloheptatriene
`compound,
`bis(diphenylvinylphenyl)anthracene,
`silicongermaniumoxide compound, silicon-based arylamine compound,
`and the like.
`On the hole transport layer, an organic luminescence layer
`is positioned. Such an organic luminescence layer is made of a
`material having a high quantum efficiency, in which holes and
`electrons which are injected from an anode and a cathode,
`respectively, are recombined so as to emit light. As a light
`emitting
`material, a
`material
`allowing
`holes and
`electrons
`transferred
`from
`a
`hole
`transport
`layer
`and
`an
`electron
`transport layer, respectively, to be combined so as to emit
`visible light is used. Preferably, a material having a high
`quantum efficiency against fluorescence or phosphorescence is
`used.
`As a material or a compound satisfying these conditions,
`for a green color, Alq3 may be used, and for a blue color,
`Balq(8-hydroxyquinoline
`beryllium
`salt),
`DPVBi(4,4'-bis(2,2-
`diphenylethenyl)-1,1'-biphenyl) based, Spiro
`material, spiro-
`DPVBi(Spiro-4,4'-bis(2,2-diphenylethenyl)-1,1'-biphenyl),
`LiPBO(2-(2-benzoxazoyl)-phenol
`lithium
`
`salt),
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000030
`
`
`
`metal
`aluminum-quinoline
`bis(diphenylvinylphenylvinyl)benzene,
`complex, imidazole, thiazol and oxazole-metal complex, or the
`like may be used. In order to improve the luminous efficiency of
`a blue color, perylene, and BczVBi(3,3'[(1,1'-biphenyl)-4,4'-
`diyldi-2,1-ethenediyl]bis(9-ethyl)-9H-carbazole;
`DSA(distrylamine)) may be doped in a small amount. For a red
`color,
`a green
`light emitting material may
`be
`doped with
`DCJTB([2-(1,1-dimethylethyl)-6-[2-(2,3,6,7-tetrahydro-1,1,7,7-
`tetramethyl-1H,5H-benzo(ij)quinolizin-9-yl)ethenyl]-4H-pyran-4-
`ylidene]-propanedinitrile) in a small amount. When a process
`such as inkjet printing, roll coating, spin coating, is used to
`form a light emitting layer, polyphenylenevinylene (PPV)-based
`polymer or poly fluorene may be used for an organic luminescence
`layer.
`On the organic luminescence layer, an electron transport
`layer is positioned. Such an electron transport layer requires a
`material which has a high efficiency for electrons injected from
`a cathode positioned thereon, and can efficiently transport the
`injected electrons. For this, a material having a high electron
`affinity,
`a
`high
`electron
`mobility,
`and
`a
`high
`electron
`stability is required. The examples of an electron transport
`material satisfying these conditions may include Al complex of
`8-hydroxyquinoline;
`complex
`including
`organic
`radical
`Alq3;
`compound; and
`hydroxyflavone-metal
`complex,
`but the
`present
`invention is not limited thereto.
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000031
`
`
`
`On the electron transport layer, an electron injection
`layer
`is
`layered.
`The
`electron
`injection
`layer
`may
`be
`manufactured by using a metal complex compound (such as Balq,
`Alq3, Be(bq)2, Zn(BTZ)2, Zn(phq)2, PBD, spiro-PBD, TPBI, and Tf-
`6P) or a low molecular material including an aromatic compound
`having an imidazole ring or a boron compound. Herein, the
`electron injection layer may be formed in a thickness range of
`100Å to 300 Å.
`On the electron injection layer, a cathode is positioned.
`Such a cathode performs a role of injecting electrons into the
`electron injection layer. As a material for the cathode, the
`same material as that used for an anode may be used. In order to
`achieve efficient electron injection, a metal having a low work
`function is more preferable. Especially, metals such as tin,
`magnesium, indium, calcium, sodium, lithium, aluminum, silver,
`or
`alloys
`thereof
`may
`be
`used.
`Further,
`a
`double-layered
`electrode such as lithiumfluoride and aluminum, lithium oxide
`and aluminum, and strontium oxide and aluminum, with a thickness
`
`of 100㎛ or less may be used.
`
`As mentioned, the compound including two or more 5-membered
`heterocycles, as described with reference to Formulas 1 to 12,
`may be used as a hole injection material, a hole transport
`material,
`a
`light
`emitting
`material,
`and/or
`an
`electron
`transport
`material
`appropriate
`for
`a
`fluorescent
`or
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000032
`
`
`
`phosphorescent device of all colors such as red, green, blue,
`white, etc., and be used as a host material for various colors
`of a phosphorescent dopant.
`be
`may
`invention
`present
`the
`to
`The
`OLED
`according
`manufactured in a front luminescent type, a rear luminescent
`type, or a both-side luminescent type according to its materials.
`Meanwhile, the present invention provides a terminal which
`includes a display device and a control part for driving the
`display device, the display device including the above described
`organic electronic device. The terminal means a wired/wireless
`communication terminal which is currently used or will be used
`in the future. The above described terminal according to the
`present invention may be a mobile communication terminal such as
`a cellular phone, and may include all kinds of terminals such as
`a PDA, an electronic dictionary, a PMP, a remote control, a
`navigation unit, a game player, various kinds of TVs, and
`various kinds of computers.
`
`Example
`Hereinafter, the present invention will be described more
`specifically
`with
`reference
`to
`Preparation
`Examples
`and
`Experimental Examples. However, the following examples are only
`for illustrative purposes and are not intended to limit the
`scope of the invention.
`Preparation Example
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000033
`
`
`
`Hereinafter, Preparation Examples or Synthesis Examples of
`the compounds including two or more 5-membered heterocycles,
`represented by Formula 6, will be described. However, since
`there are
`many
`compounds including
`two or more 5-membered
`heterocycles, represented by Formula 6, one compound or two
`compounds from among the compounds will be exemplified. The
`person skilled in the art of the invention should realize that
`other compounds including two or more 5-membered heterocycles
`can be prepared through Preparation Examples as described below
`although they are not exemplified.
`Step 1) Synthesis method of intermediate A
`[Reaction Scheme 1]
`
`(2-
`
`acid,
`
`4-bromonaphthalen-1-ylboronic
`bromophenyl)(methyl)sulfane,
`tetrakis(triphenylphophine)palladium(0) and potassium carbonate
`were dissolved in THF(tetrahydrofuran) and water(3:1), followed
`by stirred at 70℃. Upon completion of the reaction, the reaction
`product was extracted with CH2Cl2, and washed with water. From
`the extract, a small amount of water was removed by anhydrous
`MgSO4, followed by vacuum-filtration. Then, the product obtained
`after concentration of an organic solvent was recrystallized by
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000034
`
`
`
`CH2Cl2 and hexane solvent to obtain a required intermediate A
`(yield: 70%).
`Step 2) Synthesis method of intermediate B
`[Reaction Scheme 2]
`
`The intermediate A obtained from the step 1 was dissolved
`in acetic acid, and a solution obtained by dissolving hydrogen
`peroxide in acetic acid was added dropwise thereto with stirring
`for 6 hours at room temperature. Upon completion of the reaction,
`acetic acid was removed by a decompression device. Then, the
`product was
`purified
`by
`column
`chromatography
`to
`obtain
`a
`required intermediate B (yield: 92%).
`Step 3) Synthesis method of intermediate C
`[Reaction Scheme 3]
`
`The intermediate B obtained from the step 2 was dissolved
`in trifluoromethanesulfonic acid, followed by stirring for 24
`hours at room temperature. Water and pyridine (8:1) were slowly
`dropped thereto, and the reaction product was refluxed for 30
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000035
`
`
`
`minutes. The temperature of the reaction product was lowered,
`extracted with CH2Cl2, and washed with water. From the extract, a
`small amount of water was removed by anhydrous MgSO4, followed by
`vacuum-filtration.
`Then,
`the
`product
`obtained
`after
`concentration of an organic solvent was purified by column
`chromatography to obtain a required intermediate C (yield: 80%).
`Step 4) Synthesis method of intermediate D
`[Reaction Scheme 4]
`
`The intermediate C obtained from the step 3, Pd(PPh3)4, and
`K2CO3 were dissolved in anhydrous THF and a small amount of water,
`followed by reflux for 24 hours. Upon completion of the reaction,
`the reaction product was cooled to room temperature, extracted
`with CH2Cl2, and washed with water. From the extract, a small
`amount of water was removed by anhydrous MgSO4, followed by
`vacuum-filtration.
`Then,
`the
`product
`obtained
`after
`concentration of an organic solvent was purified by column
`chromatography to obtain a required intermediate D (yield: 70%).
`Step 5) Synthesis method of intermediate E
`[Reaction Scheme 5]
`
`DUK SAN NEOLUX
`EXHIBIT 1012
`PAGE 000036
`
`
`
`and
`4
`step
`the
`from
`obtained
`D
`intermediate
`The
`triphenylphosphine were dissolved in o-dichlorobenzene, followed
`by reflux for 24 hours. Upon completion of the reaction, vacuum
`distillation was carried out for removal of a solvent. Then, the
`concentrated product was purified by column chromatography to
`obtain a required intermediate E (yield: 61%).
`Synthesis Example 1: Synthesis method of compound 4
`[Reaction Scheme 6]
`
`The intermediate E obtained from the step 5, bromobiphenyl,
`NaOtBu
`were
`dissolved in a
`toluene
`Pd2(dba)3,
`P(tBu)3, and
`solvent, followed by reflux for 6 hours at 110℃. Upon completion
`of
`the reaction,
`the reaction product
`was cooled to room
`temperature, extracted with CH2Cl2, and washed with water. From
`the extract, a small amount of water was removed by anhydrous
`MgSO4, followed by vacuum-filtration. Then, the product obtained
`after concentration of an organic solvent was purified by column
`chr
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