Abstract
`Disclosed are a compound including 5-membered heterocycle,
`an organic electric element comprising the same, and a terminal
`thereof.
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000001
`
`
`Disclosed are a compound including 5-membered heterocycle,
`an organic electric element comprising the same, and a terminal
`thereof.
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000001
`
`
`
`Claims
`
`1. A compound represented by Formula below:
`
`wherein,
`(1) R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 are each
`independently selected from the group consisting of a hydrogen
`atom, a halogen atom, a cyano group, an alkoxy group, a thiol
`group, a substituted or unsubstituted C1-C50 alkyl group, a
`substituted or unsubstituted C1-C50 alkoxy group, a substituted or
`unsubstituted C1-C50 alkenyl group, a substituted or unsubstituted
`C5-C60 arylene group, a substituted or unsubstituted C5-C60 aryl
`group, a substituted or unsubstituted C5-C60 aryloxy group, a
`substituted or unsubstituted C1-C50 alkyl group 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 C5-C60 heteroaryl group
`containing at least one heteroatom selected from the group
`consisting of sulfur (S), nitrogen (N), oxygen(O), phosphorous
`(P) and silicon (Si), and a substituted or unsubstituted C5-C60
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000002
`
`
`
`heteroaryloxy group containing at least one heteroatom selected
`from the group consisting of sulfur (S), nitrogen (N), oxygen(O),
`phosphorous (P) and silicon (Si), and
`(2) Ar is substituted or unsubstituted by a C6-C60 aromatic
`compound comprising carbons.
`
`2. A compound represented by Formula below:
`
`wherein,
`(1) R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 each are
`independently selected from the group consisting of a hydrogen
`atom, a halogen atom, a cyano group, an alkoxy group, a thiol
`group, a substituted or unsubstituted C1-C50 alkyl group, a
`substituted or unsubstituted C1-C50 alkoxy group, a substituted or
`unsubstituted C1-C50 alkenyl group, a substituted or unsubstituted
`C5-C60 arylene group, a substituted or unsubstituted C5-C60 aryl
`group, a substituted or unsubstituted C5-C60 aryloxy group, a
`substituted or unsubstituted C1-C50 alkyl group 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 C5-C60 heteroaryl group
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000003
`
`
`
`containing at least one heteroatom selected from the group
`consisting of sulfur (S), nitrogen (N), oxygen(O), phosphorous
`(P) and silicon (Si), and a substituted or unsubstituted C5-C60
`heteroaryloxy group containing at least one heteroatom selected
`from the group consisting of sulfur (S), nitrogen (N), oxygen(O),
`phosphorous (P) and silicon (Si), and
`(2) HAr is substituted or unsubstituted by a C1-C60 hetero
`ring compound comprising at least one atom except carbon.
`
`3. A compound represented by Formula below:
`
`wherein,
`(1) R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 each are
`independently selected from the group consisting of a hydrogen
`atom, a halogen atom, a cyano group, an alkoxy group, a thiol
`group, a substituted or unsubstituted C1-C50 alkyl group, a
`substituted or unsubstituted C1-C50 alkoxy group, a substituted or
`unsubstituted C1-C50 alkenyl group, a substituted or unsubstituted
`C5-C60 arylene group, a substituted or unsubstituted C5-C60 aryl
`group, a substituted or unsubstituted C5-C60 aryloxy group, a
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000004
`
`
`
`substituted or unsubstituted C1-C50 alkyl group 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 C5-C60 heteroaryl group
`containing at least one heteroatom selected from the group
`consisting of sulfur (S), nitrogen (N), oxygen(O), phosphorous
`(P) and silicon (Si), and a substituted or unsubstituted C5-C60
`heteroaryloxy group containing at least one heteroatom selected
`from the group consisting of sulfur (S), nitrogen (N), oxygen(O),
`phosphorous (P) and silicon (Si), and
`(2) Ar is substituted or unsubstituted by a C6-C60 aromatic
`compound comprising carbons.
`
`4. A compound represented by Formula below:
`
`wherein,
`(1) R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 each are
`independently selected from the group consisting of a hydrogen
`atom, a halogen atom, a cyano group, an alkoxy group, a thiol
`group, a substituted or unsubstituted C1-C50 alkyl group, a
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000005
`
`
`
`substituted or unsubstituted C1-C50 alkoxy group, a substituted or
`unsubstituted C1-C50 alkenyl group, a substituted or unsubstituted
`C5-C60 arylene group, a substituted or unsubstituted C5-C60 aryl
`group, a substituted or unsubstituted C5-C60 aryloxy group, a
`substituted or unsubstituted C1-C50 alkyl group 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 C5-C60 heteroaryl group
`containing at least one heteroatom selected from the group
`consisting of sulfur (S), nitrogen (N), oxygen(O), phosphorous
`(P) and silicon (Si), and a substituted or unsubstituted C5-C60
`heteroaryloxy group containing at least one heteroatom selected
`from the group consisting of sulfur (S), nitrogen (N), oxygen(O),
`phosphorous (P) and silicon (Si),
`(2) Ar is substituted or unsubstituted by a C6-C60 aromatic
`compound comprising carbons, and
`(3) HAr is substituted or unsubstituted by a C1-C60 hetero
`ring compound comprising at least one atom except carbon.
`
`5. A compound represented by Formula below:
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000006
`
`
`
`wherein,
`(1) R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 each are
`independently selected from the group consisting of a hydrogen
`atom, a halogen atom, a cyano group, an alkoxy group, a thiol
`group, a substituted or unsubstituted C1-C50 alkyl group, a
`substituted or unsubstituted C1-C50 alkoxy group, a substituted or
`unsubstituted C1-C50 alkenyl group, a substituted or unsubstituted
`C5-C60 arylene group, a substituted or unsubstituted C5-C60 aryl
`group, a substituted or unsubstituted C5-C60 aryloxy group, a
`substituted or unsubstituted C1-C50 alkyl group 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 C5-C60 heteroaryl group
`containing at least one heteroatom selected from the group
`consisting of sulfur (S), nitrogen (N), oxygen(O), phosphorous
`(P) and silicon (Si), and a substituted or unsubstituted C5-C60
`heteroaryloxy group containing at least one heteroatom selected
`from the group consisting of sulfur (S), nitrogen (N), oxygen(O),
`phosphorous (P) and silicon (Si),
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000007
`
`
`
`(2) HAr is substituted or unsubstituted by a C1-C60 hetero
`ring compound comprising at least one atom except carbon, and
`(3) Ar is substituted or unsubstituted by a C6-C60 aromatic
`compound comprising carbons.
`
`6. A compound represented by Formula below:
`
`wherein,
`(1) R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 each are
`independently selected from the group consisting of 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
`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
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000008
`
`
`
`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),
`and
`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), and
`(2) HAr is substituted or unsubstituted by a hetero ring
`compound having 1 to 60 carbon atoms and comprising at least one
`atom except carbon.
`
`7. The compound as claimed in any one of claims 1 to 3,
`wherein R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, R7
`and R8, and R9 and R10 each are able to form a saturated or
`unsaturated ring together with an adjacent group.
`
`8. The compound as claimed in any one of claims 1 to 3,
`being any one of the compounds below:
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000009
`
`
`
`-2
`
`-3
`
`-4
`
`-5
`
`1-12
`
`1-13
`
`1-14
`
`1-15
`
`1-16
`
`-17
`
`-18
`
`-19
`
`-20
`
`N C
`
`»S
`
`N
`
`(/3
`
`N ®0
`
`N 6
`
`0
`
`2.
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000010
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000010
`
`
`
`12
`
`2-13
`
`2-14
`
`2-15
`
`2-16
`
`2-17
`
`3-
`
`3
`
`3-10
`
`3
`
`3-12
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 00001 1
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000011
`
`
`
`3-13
`
`3-14
`
`3-15
`
`3-16
`
`-17
`
`-18
`
`.3“D8
`000
`
`01:0D8
`
`01:-
`
`19
`
`-20
`
`21
`
`0
`
`0
`
`O
`
`“=-
`
`-22
`
`01:-
`
`-23
`
`01:-
`
`-24
`
`-25
`
`-25
`
`-27
`
`-28
`
`-29
`
`-30
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000012
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000012
`
`
`
`4
`
`4-10
`
`4-11
`
`-13
`
`14
`
`15
`
`16
`
`17
`
`18
`
`19
`
`-20
`
`-21
`
`-22
`
`23
`
`-24
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000013
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000013
`
`
`
`ooo
`0
`
`N
`N/
`\
`N
`
`I
`
`N
`“*1”
`©*‘~*©
`
`N
`
`/
`\1
`“ 0 O
`
`N
`
`N2\N
`\|
`
`O
`
`-10
`
`5.
`
`-12
`
`13
`
`5-14
`
`15
`
`5-16
`
`5-17
`
`-18
`
`1
`
`6
`
`-6
`
`10
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000014
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000014
`
`
`
`.
`
`9. An organic electric element comprising one or more
`organic material layers comprise the compound as claimed in any
`one of claims 1 to 8.
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000015
`
`
`
`10. The organic electric element as claimed in claim 9,
`wherein the organic material layers are formed by a soluble
`process of the compound.
`
`11. The organic electric element as claimed in claim 9,
`wherein
`the
`organic
`electric
`element
`is
`an
`organic
`light
`emitting diode in which a first electrode, said one or more
`organic material layers, and a second electrode are sequentially
`layered.
`
`12. The organic electric element as claimed in claim 11,
`wherein the organic material layers comprise a light emitting
`layer, and in the light emitting layer, the compound is used as
`a host material.
`
`13. A terminal comprising a display device, which comprises
`the organic electric element as claimed in claim 9, and a
`control unit for driving the display device.
`
`14. The terminal as claimed in claim 13, wherein the
`organic electric element comprises at least one of 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.
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000016
`
`
`
`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 respective 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, and
`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 1010
`PAGE 000017
`
`
`
`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 1010
`PAGE 000018
`
`
`
`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
`and
`an
`electron
`injection
`material
`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 1010
`PAGE 000019
`
`
`
`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 1010
`PAGE 000020
`
`
`
`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
`define
`an
`essence,
`order
`or
`sequence
`of
`a
`corresponding
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000021
`
`
`
`corresponding
`distinguish the
`to
`merely
`used
`component but
`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, and R10 are each
`independently selected from the group consisting of 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
`50
`carbon
`atoms,
`a
`substituted
`or
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000022
`
`
`
`unsubstituted arylene group having 5 to 60 carbon atoms, a
`substituted or unsubstituted 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 atom and s
`containing at least one heteroatom selected from the group
`consisting of sulfur (S), nitrogen (N), oxygen(O), phosphorous
`(P)
`and
`silicon
`(Si),
`and
`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) Each of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and
`R7, R7 and R8, and R9 and R10 is able to form a saturated or
`unsaturated ring together with an adjacent group,
`(3) Ar may be substituted or unsubstituted by a C6-C60
`aromatic compound having 2 to 60 carbon atoms and comprising
`carbons, and
`(4) the compound having the structural formula above 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.
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000023
`
`
`
`[Formula 2]
`
`Wherein,
`(5) R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each equally
`defined as in Formula 1.
`(6) Each of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and
`R7, R7 and R8, and R9 and R10 is able to form a saturated or
`unsaturated ring together with an adjacent group,
`(7) HAr may be substituted or unsubstituted by a hetero
`ring compound having 1 to 60 carbon atoms and comprising at
`least one atom except carbon, and
`(8) the compound having the structural formula above may be
`used for a soluble process.
`In accordance with another aspect of the present invention,
`there is provided a compound represented by Formula 3 below.
`[Formula 3]
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000024
`
`
`
`Wherein,
`(9) R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each equally
`defined as in Formula 1.
`(10) Each of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6
`and R7, R7 and R8, and R9 and R10 is able to form a saturated or
`unsaturated ring together with an adjacent group,
`(11) Ar may be substituted or unsubstituted by a C6-C60
`aromatic compound comprising carbons, and
`(12) the compound having the structural formula above may
`be used for a soluble process.
`In accordance with another aspect of the present invention,
`there is provided a compound represented by Formula 4 below.
`[Formula 4]
`
`Wherein,
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000025
`
`
`
`(13) R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each
`equally defined as in Formula 1.
`(14) Each of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6
`and R7, R7 and R8, and R9 and R10 is able to form a saturated or
`unsaturated ring together with an adjacent group,
`(15) Ar may be substituted or unsubstituted by a aromatic
`compound having 6 to 60 carbon atoms and comprising carbons,
`(16) HAr may be substituted or unsubstituted by a hetero
`ring compound having 1 to 60 carbon atoms and comprising at
`least one atom except carbon, and
`(17) the compound having the structural formula above may
`be used for a soluble process.
`In accordance with another aspect of the present invention,
`there is provided a compound represented by Formula 5 below.
`[Formula 5]
`
`Wherein,
`(18) R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each
`equally defined as in Formula 1.
`(19) Each of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000026
`
`
`
`and R7, R7 and R8, and R9 and R10 is able to form a saturated or
`unsaturated ring together with an adjacent group,
`(20) HAr may be substituted or unsubstituted by a hetero
`ring compound having 1 to 60 carbon atoms and comprising at
`least one atom except carbon,
`(21) Ar may be substituted or unsubstituted by a C6-C60
`aromatic compound having 6 to 60 carbon atoms and comprising
`carbons, and
`(22) the compound having the structural formula above may
`be used for a soluble process.
`In accordance with another aspect of the present invention,
`there is provided a compound represented by Formula 6 below.
`[Formula 6]
`
`(23) R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 may each be
`equally defined as in Formula 1.
`(24) Each of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6
`and R7, R7 and R8, and R9 and R10 is able to form a saturated or
`unsaturated ring together with an adjacent group,
`(25) HAr may be substituted or unsubstituted by a hetero
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000027
`
`
`
`ring compound having 1 to 60 carbon atoms and comprising at
`least one atom except carbon, and
`(26) the compound having the structural formula above 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 6, may
`include compounds represented by Formula 7. However, the present
`invention is not limited thereto.
`[Formula 7]
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000028
`
`
`
`[Formula 8]
`
`[Formula 9]
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000029
`
`
`
`3-
`
`3-12
`
`Na3
`
`3-13
`
`3-14
`
`3-15
`
`3
`
`3-17
`
`-18
`
`000m3fine
`
`01:Oes
`
`ON:
`
`3-19
`
`-20
`
`-21
`
`0
`
`0
`
`O
`
`N:
`
`22
`
`06¢
`
`01:
`
`-23
`
`3-24
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000030
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000030
`
`
`
`[Formula 10]
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000031
`
`
`
`[Formula 11]
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000032
`
`
`
`[Formula 12]
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000033
`
`
`
`There exist various organic electric devices which employ
`compounds including two or more 5-membered heterocycles, as
`described with reference to Formulas 1 to 12, 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 12, 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
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000034
`
`
`
`laser diode, and the like.
`As one example of the organic electric devices in which
`compounds including two or more 5-membered heterocycles, as
`described with reference to Formulas 1 to 12, 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 12.
`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.
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000035
`
`
`
`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
`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
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000036
`
`
`
`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.
`The compound including two or more 5-membered heterocycles,
`as described with reference to Formulas 1 to 12,
`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
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000037
`
`
`
`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
`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
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000038
`
`
`
`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
`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
`
`DUK SAN NEOLUX
`EXHIBIT 1010
`PAGE 000039
`
`
`
`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
`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
`
Accessing this document will incur an additional charge of $.
After purchase, you can access this document again without charge.
Accept $ Charge
Still Working On It
This document is taking longer than usual to download. This can happen if we need to contact the court directly to obtain the document and their servers are running slowly.
Give it another minute or two to complete, and then try the refresh button.
A few More Minutes ... Still Working
It can take up to 5 minutes for us to download a document if the court servers are running slowly.
Thank you for your continued patience.
This document could not be displayed.
We could not find this document within its docket. Please go back to the docket page and check the link. If that does not work, go back to the docket and refresh it to pull the newest information.
Your account does not support viewing this document.
You need a Paid Account to view this document. Click here to change your account type.
Your account does not support viewing this document.
Set your membership
status to view this document.
With a Docket Alarm membership, you'll
get a whole lot more, including:
- Up-to-date information for this case.
- Email alerts whenever there is an update.
- Full text search for other cases.
- Get email alerts whenever a new case matches your search.
One Moment Please
The filing “” is large (MB) and is being downloaded.
Please refresh this page in a few minutes to see if the filing has been downloaded. The filing will also be emailed to you when the download completes.
Your document is on its way!
If you do not receive the document in five minutes, contact support at support@docketalarm.com.
Sealed Document
We are unable to display this document, it may be under a court ordered seal.
If you have proper credentials to access the file, you may proceed directly to the court's system using your government issued username and password.
Access Government Site
