Specification
`
`Material for organic electroluminescence device and organic
`
`electroluminescence device using the same
`
`[Technical Field]
`
`[0001] (cid:9)
`
`The present invention relates to a material for an
`
`organic electroluminescence device and an organic
`
`electroluminescence device using the material, in particular, an
`
`organic electroluminescence device, which shows high luminous
`
`efficiency, is free of any pixel defect, and has a long lifetime,
`
`and a material for an organic electroluminescence device for
`
`realizing the device.
`
`[Background Art]
`
`[0002] (cid:9)
`
`An organic electroluminescence device (hereinafter,
`
`"electroluminescence" may be abbreviated as "EL") is a spontaneous
`
`light emitting device which utilizes the principle that a fluorescent
`
`substance emits light by energy of recombination of holes injected
`
`from an anode and electrons injected from a cathode when an electric
`
`field is applied. Since an organic EL device of the laminate type
`
`driven under a low electric voltage was reported, many studies have
`
`been conducted on organic EL devices using organic materials as
`
`the constituent materials. The devices of the laminate type use
`
`tris (8-quinolinolato) aluminum for a light emitting layer and a
`
`1
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000001
`
`
`
`Material for organic electroluminescence device and organic
`
`electroluminescence device using the same
`
`[Technical Field]
`
`[0001] (cid:9)
`
`The present invention relates to a material for an
`
`organic electroluminescence device and an organic
`
`electroluminescence device using the material, in particular, an
`
`organic electroluminescence device, which shows high luminous
`
`efficiency, is free of any pixel defect, and has a long lifetime,
`
`and a material for an organic electroluminescence device for
`
`realizing the device.
`
`[Background Art]
`
`[0002] (cid:9)
`
`An organic electroluminescence device (hereinafter,
`
`"electroluminescence" may be abbreviated as "EL") is a spontaneous
`
`light emitting device which utilizes the principle that a fluorescent
`
`substance emits light by energy of recombination of holes injected
`
`from an anode and electrons injected from a cathode when an electric
`
`field is applied. Since an organic EL device of the laminate type
`
`driven under a low electric voltage was reported, many studies have
`
`been conducted on organic EL devices using organic materials as
`
`the constituent materials. The devices of the laminate type use
`
`tris (8-quinolinolato) aluminum for a light emitting layer and a
`
`1
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000001
`
`
`
`triphenyldiamine derivative for a hole transporting layer.
`
`Advantages of the laminate structure are that the efficiency of
`
`hole injection into the light emitting layer can be increased, that
`
`the efficiency of forming exciton which are formed by blocking and
`
`recombining electrons injected from the cathode can be increased,
`
`and that exciton formedwithin the light emitting layer can be enclosed.
`
`As described above, for the structure of the organic EL device,
`
`a two-layered structure having a hole transporting (injecting) layer
`
`and an electron transporting light emitting layer and a three-layered
`
`structure having a hole transporting (injecting) layer, a light
`
`emitting layer, and an electron transporting (injecting) layer are
`
`well known. To increase the efficiency of recombination of injected
`
`holes and electrons in the devices of the laminate type, the structure
`
`of the device and the process for forming the device have been studied.
`
`[0003] (cid:9)
`
`As the light emitting material of the organic EL device,
`
`chelate complexes such as tris (8-quinolinolato) aluminum complexes,
`
`coumarine derivatives, tetraphenylbutadiene derivatives,
`
`distyrylarylene derivatives, and oxadiazole derivatives are known.
`
`It is reported that light in the visible region ranging from blue
`
`light to red light can be obtained by using these light emitting
`
`materials, and development of a device exhibiting color images is
`
`expected.
`
`In addition, it has been recently proposed that a
`
`phosphorescent material as well as a fluorescent material be utilized
`
`2
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000002
`
`
`
`in the light emitting layer of an organic EL device. High luminous
`
`efficiency is achieved by utilizing the singlet and triplet states
`
`of an excited state of an organic phosphorescent material in the
`
`light emitting layer of an organic EL device. Upon recombination.
`
`of an electron and a hole in an organic EL device, singlet excitons
`
`and triplet excitons may be produced at a ratio of 1:3 owing to
`
`a difference in spin multiplicity between the singlet and triplet
`
`excitons , so the use of a phosphorescent material may achieve luminous
`
`efficiency three to four times as high as that of a device using
`
`fluorescence alone.
`
`[0004] (cid:9)
`
`Patent Documents 1 to 7 are exemplary inventions each
`
`describing such materials for an organic EL device.
`
`Patent Document 1 describes a compound using, as a mother
`
`skeleton, a structure obtained by crosslinking a terphenylene
`
`skeleton with, for example, a carbon atom, nitrogen atom, or oxygen
`
`atom. The document, which mainly discloses data indicative of the
`
`potential of the compound to serve as a hole transporting material,
`
`describes that the compound is used as a host material for a
`
`phosphorescent material in a light emitting layer. However, the
`
`description is limited to a red phosphorescent device, and the
`
`luminous efficiency of the device is not high enough for the device
`
`to be put into practical use.
`
`Patent Document 2 describes an indolocarbazole compoundhaving
`
`a substituent on a nitrogen atom or on an aromatic ring . The document
`
`3
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000003
`
`
`
`recommends that the compound be used as a hole transporting material ,
`
`and describes that a thermally and morphologically stable, thin
`
`hole transporting layer can be prepared from the compound. However,
`
`the document does not describe data indicative of the usefulness
`
`of the compound as a host material or electron transporting material
`
`to be used together with a phosphorescent material.
`
`Patent Document 3 describes indolocarbazole compounds each
`
`having a substituent on a nitrogen atom or on an aromatic ring.
`
`The document discloses data on a green light emitting device using
`
`any one of those compounds as a host material for a phosphorescent
`
`material in its light emitting layer. However, a high voltage must
`
`be applied to the device to drive the device, and the device shows
`
`low luminous efficiency, so the device cannot be sufficiently put
`
`into practical use.
`
`Patent Document 4 describes indolocarbazole compounds each
`
`having a substituent. The document describes that each of the
`
`compounds functions as a host material for a phosphorescent material
`
`in a light emitting layer. However, each of those compounds is
`
`characterized in that the compound has a dimer or trimer structure
`
`through a linking group, and each of the compounds tends to have
`
`a large molecular weight. The document discloses data on a green
`
`phosphorescent device using any one of those compounds, but all
`
`the compounds used each have a large molecular weight of 800 or
`
`more. The efficiency with which a material having a large molecular
`
`4
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000004
`
`
`
`weight is deposited in a vacuum is poor, and the material may decompose
`
`owing to heating for a long time period, so the material may be
`
`insufficient in terms of practical use.
`
`Patent Documents 5 and 6 describe indenofluorene compounds
`
`each having a substituent on an aromatic ring, and describe that
`
`each of the compounds functions as a fluorescent material in a light
`
`emitting layer. However, none of the documents describes data
`
`indicative of the usefulness of each of the compounds as a host
`
`material or electron transporting material to be used together with
`
`a phosphorescent material.
`
`Patent Document 7 describes compounds each using, as a mother
`
`skeleton, a structure obtained by crosslinking a terphenylene
`
`skeleton with a sulfur atom, boron atom, or phosphorus atom. The
`
`document describes that each of those compounds has excellent
`
`oxidation resistance, and allows the formation of an organic
`
`semiconductor active layer by an application method. However, the
`
`document does not describe data indicative of the usefulness of
`
`each of the compounds as a host material or electron transporting
`
`material to be used together with a fluorescent material or
`
`phosphorescent material.
`
`[0005] (cid:9)
`
`Patent Document 1: WO 2006/122630
`
`Patent Document 2: EP 0909787
`
`Patent Document 3: WO 2007/063796
`
`Patent Document 4: WO 2007/063754
`
`5
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000005
`
`
`
`Patent Document 5: US 2002/0132134
`
`Patent Document 6: US 2003/0044646
`
`Patent Document 7: JP 2008-81494
`
`[Disclosure of the Invention]
`
`[Problems to be solved by the Invention]
`
`[0006] (cid:9)
`
`The present invent ion has been made with a view to solving
`
`the above problems, and an object of the present invention is to
`
`provide an organic EL device which shows high luminous efficiency,
`
`is free of any pixel defect, and has a long lifetime, and a material
`
`for an organic EL device for realizing the device.
`
`[Means for solving the Problems]
`
`[0007] (cid:9)
`
`The inventors of the present invention have made
`
`extensive studies with a view to achieving the above object. As
`
`a result, the inventors have found that the above object can be
`
`achieved by using a compound having a n-conjugated heteroacene
`
`skeleton crosslinked with a carbon atom, nitrogen atom, oxygen atom,
`
`or sulfur atom as a material for an organic EL device. Thus, the
`
`inventors have completed the present invention.
`
`[0008] (cid:9)
`
`That is, the present invention provides a material for
`
`an organic EL device represented by the following formulae (1) or
`
`(2) .
`
`6
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000006
`
`
`
`X310
`
`Ar3
`z
`X2Iq
`
`L2-A2
`
`S
`
`
`X310
`
`Ar3 (cid:9)
`
`
`
`L3
`
`/
`
`X2Iq _s
`
`n
`
`(1) (cid:9)
`
`(2)
`
`[0009] (cid:9)
`
`[In the formulae (1) and (2) , Ar1, Ar2 , and Ar3 each
`
`independently represent a substituted or unsubstituted aromatic
`
`hydrocarbon group having a ring formed of 6 to 24 carbon atoms or
`
`a substituted or unsubstituted aromatic heterocyclic group having
`
`a ring formed of 3 to 24 atoms, provided that, Art , Ar2 , and Ar3
`
`each may have one substituent Y or multiple substituents Ys, in
`
`the case of multiple substituents Ys, the substituent Ys may be
`
`different from each other, Y represents an alkyl group having 1
`
`to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group
`
`having a ring formed of 3 to 20 carbon atoms, an alkoxy group having
`
`1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms,
`
`a silyl group having 3 to 20 carbon atoms, a substituted or
`
`unsubstituted aromatic hydrocarbon group having a ring formed of
`
`6 to 24 carbon atoms, or a substituted or unsubstituted aromatic
`
`heterocyclic group which has a ring formed of 3 to 24 atoms and
`
`which is linked with Art , Ar2 , or Ar3 through a carbon-carbon bond.
`
`In the formulae (1) and (2) , X1, X2 X3 and X4 each independently
`
`represent 0, S, N-R1 or CR2R3 (N atom of N-R, or C atom of CR2R3 binds
`
`7
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000007
`
`
`
`to Ari, Ar2 , or Ara ) -
`
`In the formulae (1) and (2) , R1, R2 , and R3 each independently
`
`represent an alkyl group having 1 to 20 carbon atoms, a substituted
`
`or unsubstituted cycloalkyl group having a ring formed of 3 to 20
`
`carbon atoms, an aralkyl group having 7 to 24 carbon atoms, a silyl
`
`group having 3 to 20 carbon atoms, a substituted or unsubstituted
`
`aromatic hydrocarbon group having a ring formed of 6 to 24 carbon
`
`atoms, or a substituted or unsubstituted aromatic heterocyclic group
`
`having a ring formed of 3 to 24 atoms, provided that, when both
`
`X1 and X2 represent N-R1, o and p each represent 0, and q represents
`
`1, or when both Xi and X3 represent N-R1, p and q each represent
`
`0, and o represents 1, at least one Ri represents a substituted
`
`or unsubstituted, monovalent fused aromatic heterocyclic group
`
`having a. ring formed of 8 to 24 atoms.
`
`In the formulae (1) and (2) o, p, and q each represent 0 or
`
`1 and s represents 1, 2, or 3. n represents 2, 3, or 4, and the
`
`material represented by the formula (2) includes a dimer using L3
`
`as a linking group for n = 2, a trimer using L3 as a linking group
`
`for n = 3, or a tetramer using L3 as a linking group for n = 4.
`
`In the formulae (1) and (2) , Li represents a single bond, an
`
`alkyl or alkylene group having 1 to 20 carbon atoms, a substituted
`
`or unsubstituted cycloalkyl or cycloalkylene group having a ring
`
`formed of 3 to 20 carbon atoms, a monovalent or divalent silyl group
`
`having 2 to 20 carbon atoms, a substituted or unsubstituted,
`
`8
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000008
`
`
`
`monovalent or divalent aromatic hydrocarbon group having a ring
`
`formed of 6 to 24 carbon atoms, or a substituted or unsubstituted,
`
`monovalent or divalent aromatic heterocyclic group which has a ring
`
`formed of 3 to 24 atoms and which is linked with Art through a
`
`carbon-carbon bond.
`
`In the formula (1) , L2 represents a single bond, an alkyl or
`
`alkylene group having 1 to 20 carbon atoms, a substituted or
`
`unsubstituted cycloalkyl or cycloalkylene group having a ring formed
`
`of 3 to 20 carbon atoms, a monovalent or divalent silyl group having
`
`2 to 20 carbon atoms, a substituted or unsubstituted, monovalent
`
`or divalent aromatic hydrocarbon group having a ring formed of 6
`
`to 24 carbon atoms, or a substituted or unsubstituted, monovalent
`
`or divalent aromatic heterocyclic group which has a ring formed
`
`of 3 to 24 atoms and which is linked with Ara through a carbon-carbon
`
`bond, provided that , when both X1 and X2 represent CR2R3 , o and p
`
`each represent 0, q represents 1, and both L1 and L2 represent
`
`substituted or unsubstituted, monovalent or divalent aromatic
`
`hydrocarbon groups each having a ring formed of 6 to 24 carbon atoms,
`
`or when both X1 and X3 represent CR2R3 , p and q each represent 0,
`
`o represents 1, and both L1 and L2 represent substituted or
`
`unsubstituted, monovalent or divalent aromatic hydrocarbon groups
`
`each having a ring formed of 6 to 24 carbon atoms, a case where
`
`L1 and L2 are simultaneously linked at para positions with respect
`
`to Are is excluded.
`
`9
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000009
`
`
`
`In the formula (2) , when n represents 2, L3 represents a single
`
`bond, an alkylene group having 1 to 20 carbon atoms, a substituted
`
`or unsubstituted cycloalkylene group having a ring formed of 3 to
`
`20 carbon atoms, a divalent silyl group having 2 to 20 carbon atoms,
`
`a substituted or unsubstituted, divalent aromatic hydrocarbon group
`
`having a ring formed of 6 to 24 carbon atoms, or a substituted or
`
`unsubstituted, divalent aromatic heterocyclic group which has a
`
`ring formed of 3 to 24 atoms and which is linked with Ar3 through
`
`a carbon-carbon bond, when n represents 3, L3 represents a trivalent
`
`alkane having 1 to 20 carbon atoms, a substituted or unsubstituted,
`
`trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms,
`
`a trivalent silyl group having 1 to 20 carbon atoms, a substituted
`
`or unsubstituted, trivalent aromatic hydrocarbon group having a
`
`ring formed of 6 to 24 carbon atoms , or a substituted or unsubstituted,
`
`trivalent aromatic heterocyclic group which has a ring formed of
`
`3 to 24 atoms and which is linked with Ar3 through a carbon-carbon
`
`bond, or when n represents 4, L3 represents a tetravalent alkane
`
`having 1 to 20 carbon atoms, a substituted or unsubstituted,
`
`tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms,
`
`a silicon atom, a substituted or unsubstituted, tetravalent aromatic
`
`hydrocarbon group having a ring formed of 6 to 24 carbon atoms,
`
`or a substituted or unsubstituted, tetravalent aromatic heterocyclic
`
`group which has a. ring formed of 3 to 24 atoms and which is linked
`
`with Ar3 through a carbon-carbon bond, provided that, when both X1
`
`10
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000010
`
`
`
`and X2 represent CR2R3 , o and p each represent 0, q represents 1,
`
`and both L1 and L2 represent substituted or unsubstituted, monovalent,
`
`divalent, trivalent, or tetravalent aromatic hydrocarbon groups
`
`each having a ring formed of 6 to 24 carbon atoms, or when both
`
`X1 and X3 represent CR2R3 , p and q each represent 0, o represents
`
`1, and both L1 and L3 represent substituted or unsubstituted,
`
`monovalent, divalent, trivalent, or tetravalent aromatic
`
`hydrocarbon groups each having a ring formed of 6 to 24 carbon atoms,
`
`a case where L1 and L3 are simultaneously linked at para positions
`
`with respect to Are is excluded.
`
`In the formulae (1) and (2) , Al represents a hydrogen atom,
`
`a substituted or unsubstituted cycloalkyl group having a ring formed
`
`of 3 to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms,
`
`a substituted or unsubstituted aromatic hydrocarbon group having
`
`a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted
`
`aromatic heterocyclic group which has a ring formed of 3 to 24 atoms
`
`and which is linked with L1 through a carbon-carbon bond, provided
`
`that, when L1 represents an alkyl or alkylene group having 1 to 20
`
`carbon atoms, a case where Al represents a hydrogen atom is excluded.
`
`In the formula (1) , A2 represents a hydrogen atom, a substituted
`
`or unsubstituted cycloalkyl group having a ring formed of 3 to 20
`
`carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted
`
`or unsubstituted aromatic hydrocarbon group having a ring formed
`
`of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic
`
`11
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000011
`
`
`
`heterocyclic group which has a ring formed of 3 to 24 atoms and
`
`which is linked with L2 through a carbon-carbon bond, provided that,
`
`when L2 represents an alkyl or alkylene group having 1 to 20 carbon
`
`atoms, a case where A2 represents a hydrogen atom is excluded, and,
`
`when Xi and X2 each represent 0, S, or CR2R3 , o and p each represent
`
`0, q represents 1, and both L1 and L2 represent single bonds, or
`
`when both Xi and X3 each represent 0, S, or CR2R3 , p and q each represent
`
`0, o represents 1, and both L1 and L2 represent single bonds, a case
`
`where Al and A2 simultaneously represent hydrogen atoms is excluded;
`
`In the formulae (1) and (2) , A1, A2, L1, L2 , and L3 are each
`
`free of any carbonyl group.
`
`[0010] (cid:9)
`
`A case where the formula (1) has a structure represented
`
`by the following general formula (3) is excluded,
`
`-- .......„0-12-A2
`\ C k
`Y3
`
`( 3 )
`
`provided that, X1, x2, Al , A2. L1, and L2 in the formula (3)
`
`has the same meaning X1, X2, A1, A2 / L1, and L2 in the formula (1) ,
`
`respectively.
`
`In the formula (3) , Y1, Y2 , and Y3 each represent an alkyl group
`
`having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl
`
`group having a ring formed of 3 to 20 carbon atoms, an alkoxy group
`
`having 1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon
`
`12
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000012
`
`
`
`atoms, a silyl group having 3 to 20 carbon atoms, a substituted
`
`or unsubstituted aromatic hydrocarbon group having a ring formed
`
`of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic
`
`heterocyclic group which has a ring formed of 3 to 24 atoms and
`
`which is linked with a benzene ring a, b, or c through a carbon-carbon
`
`bond, the number of each of Y1 and Y3 is 0, 1, 2, or 3, and the number
`
`of Y2 is 0, 1, or 2.
`
`[0011] (cid:9)
`
`A case where the formula (2) has a structure represented
`
`by the following general formula (4) is excluded,
`
`;\a/ (cid:9)
`
`X1
`
`(4)
`
`L3
`
`\CA
`Y3
`- n
`
`provided that, X1, X2, A1, L1, L3 , and n in the formula (4)
`
`has the same meaning X1, X2, A1, L1, L3 , and n in the formula (2) ,
`
`respectively.
`
`In the formula (4) , Y1, Y2 , and Y3 each represent an alkyl group
`
`having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl
`
`group having a ring formed of 3 to 20 carbon atoms, an alkoxy group
`
`having 1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon
`
`atoms, a silyl group having 3 to 20 carbon atoms, a substituted
`
`or unsubstituted aromatic hydrocarbon group having a ring formed
`
`of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic
`
`heterocyclic group which has a ring formed of 3 to 24 atoms and
`
`13
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000013
`
`
`
`which is linked with the benzene ring a, b, or c through a carbon-carbon
`
`bond, the number of each of Y1 and Y3 iS 0 , 1, 2, or 3, and the number
`
`of Y2 is 0, 1, or 2.]
`
`[0012] (cid:9)
`
`In addition, the present invention provides an organic
`
`EL device having one or more organic thin film layers including
`
`a light emitting layer between a cathode and an anode in which at
`
`least one layer of the organic thin film layers contains a material
`
`for an organic EL device as a compound having a n-conjugated
`
`heteroacene skeleton crosslinked with a carbon atom, nitrogen atom,
`
`oxygen atom, or sulfur atom. A material for an organic EL device
`
`represented by the above formula (1) or (2) is preferably used as
`
`the material for an organic EL device of the present invention.
`
`Further, the material for an organic EL device is effective
`
`also as a material for an organic electron device such as an organic
`
`solar cell, organic semiconductor laser, a sensor using organic
`
`matter, or an organic TFT.
`
`[Effects of the Invention]
`
`[0013] (cid:9)
`
`According to the present invention, there can be provided
`
`an organic EL device which shows high luminous efficiency, is free
`
`of any pixel defect, and has a long lifetime, and a material for
`
`an organic EL device for realizing the device.
`
`[Best Mode for carrying out the Invention]
`
`14
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000014
`
`
`
`[0014] (cid:9)
`
`A material for an organic EL device of the present
`
`invention is represented by the following general formula (1) or
`
`(2).
`
`L2 A2
`
`Ar3
`:X
`cl _s
`
`( 1 ) (cid:9)
`
`X,p
`
`X21.1:::
`
`Ai—Li—A\
`
`illikr3
`
`L3
`
`2,
`X
`
`_ (cid:9)
`
`_s
`—n
`
`Xi
`
`( 2 )
`
`[0015]
`
`[In the formulae (1) and (2) , Are , Ar2 , and Ar3 each
`
`independently represent a substituted or unsubstituted aromatic
`
`hydrocarbon group having a ring formed of 6 to 24 carbon atoms or
`
`a substituted or unsubstituted aromatic heterocyclic group having
`
`a ring formed of 3 to 24 atoms, provided that, Ari , Ar2 , and Ar3
`
`each may have one substituent Y or multiple substituents Ys, in
`
`the case of multiple substituents Ys, the substituent Ys may be
`
`different from each other, Y represents an alkyl group having 1
`
`to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group
`
`having a ring formed of 3 to 20 Carbon atoms, an alkoxy group having
`
`1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms,
`
`a silyl group having 3 to 20 carbon atoms, a substituted or
`
`unsubstituted aromatic hydrocarbon group having a ring formed of
`
`6 to 24 carbon atoms, or a substituted or unsubstituted aromatic
`
`heterocyclic group which has a ring formed of 3 to 24 atoms and
`
`15
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000015
`
`(cid:9)
`
`
`which is linked with An., Are , or Ara through a carbon-carbon bond.
`
`In the formulae (1) and (2) , X1, X2 X3 and X4 each independently
`
`represent 0, S, N-R1, or CR2R3 .
`
`In the formulae (1) and (2) , R1, R2, and R3 each independently
`
`represent an alkyl group having 1 to 20 carbon atoms, a substituted
`
`or unsubstituted cycloalkyl group having a ring formed of 3 to 20
`
`carbon atoms, an aralkyl group having 7 to 24 carbon atoms, a silyl
`
`group having 3 to 20 carbon atoms, a substituted or unsubstituted
`
`aromatic hydrocarbon group having a ring formed of 6 to 24 carbon
`
`atoms, or a substituted or unsubstituted aromatic heterocyclic group
`
`having a ring formed of 3 to 24 atoms, provided that, when both
`
`X1 and X2 represent N-R1, o and p each represent 0, and q represents
`
`1, or when both X1 and X3 represent N-R1, p and q each represent
`
`0, and o represents 1, at least one R1 represents a substituted or
`
`unsubstituted, monovalent fused aromatic heterocyclic group having
`
`a ring formed of 8 to 24 atoms.
`
`In the formulae (1) and (2) , a, p, and q each represent 0 or
`
`1, s represents 1, 2, or 3, when s represents 2 or 3, and the general
`
`formulae (1) and (2) are each represented as the following.
`
`[00161 (cid:9)
`
`When s represents 2
`
`p
`
`ri-Ar2-A\ -Ar —L2—A2
`3
`A1-L1-A
`
`X/1 1121q)\X21q
`\
`
`( 1 ) (cid:9)
`
`16
`
`X3I0 [X30
`I
`
`L3
`
`rX2Iq 1X21q
`
`n
`
`[ (cid:9)
`
`\
`
`( 2 )
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000016
`
`
`
`When s represents 3
`
`It+ X (3),)( ;)/,X c,
`
`Ixdp IX31 0 [X310 (cid:9)
`
`310
`
`A1-1-1— A r\.:•17/Ar2 fr3 (cid:9)
`
`r3 fr3—L2 -A2
`
`
`
`A1—L1—Ar..1 Ar2 fr3 fr3 fr3 7
`
`L3
`
`)\X21q )2.1c1 )X2Iq
`
`( 1 ) (cid:9)
`
`Xi )X21q))(21q)\X2.1q
`
`n
`
`( 2 )
`
`[0017]
`
`n represents 2, 3, or 4, and the material represented
`
`by the formula (2) includes a dimer using L3 as a linking group for
`
`n = 2, a trimer using L3 as a linking group for n = 3, or a tetramer
`
`using L3 as a linking group for n = 4.
`
`In the formulae (1) and (2) , L1 represents a single bond, an
`
`alkyl or alkylene group having 1 to 20 carbon atoms, a substituted
`
`or unsubstituted cycloalkyl or cycloalkylene group having a ring
`
`formed of 3 to 20 carbon atoms, a monovalent or divalent silyl group
`
`having 2 to 20 carbon atoms, a substituted or unsubstituted,
`
`monovalent or divalent aromatic hydrocarbon group having a ring
`
`formed of 6 to 24 carbon atoms, or a substituted or unsubstituted,
`
`monovalent or divalent aromatic heterocyclic group which has a ring
`
`formed of 3 to 24 atoms and which is linked with An. through a
`
`carbon-carbon bond.
`
`In the formula (1), L2 represents a single bond, an alkyl or
`
`alkylene group having I to 20 carbon atoms, a substituted or
`
`unsubstituted cycloalkyl or cycloalkylene group having a ring formed
`
`of 3 to 20 carbon atoms, a monovalent or divalent silyl group having
`
`2 to 20 carbon atoms, a substituted or unsubstituted, monovalent
`
`17
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000017
`
`(cid:9)
`
`
`or divalent aromatic hydrocarbon group having a ring formed of 6
`
`to 24 carbon atoms, or a substituted or unsubstituted, monovalent
`
`or divalent aromatic heterocyclic group which has a ring formed
`
`of 3 to 24 atoms and which is linked with Ar3 through a carbon-carbon
`
`bond, provided that, when both X1 and X2 represent CR2R3 , o and p
`
`each represent 0, q represents 1, and both L1 and L2 represent
`
`substituted or unsubstituted, monovalent or divalent aromatic
`
`hydrocarbon groups each having a ring formed of 6 to 24 carbon atoms,
`
`or when both X1 and X3 represent CR2R3 , p and q each represent 0,
`
`o represents 1, and both L1 and L2 represent substituted or
`
`unsubstituted, monovalent or divalent aromatic hydrocarbon groups
`
`each having a ring formed of 6 to 24 carbon atoms, a case where
`
`L1 and L2 are simultaneously linked at para positions with respect
`
`to Are is excluded.
`
`In the formula (2) , when n represents 2, L3 represents a single
`
`bond, an alkylene group having 1 to 20 carbon atoms, a substituted
`
`or unsubstituted cycloalkylene group having a ring formed of 3 to
`
`20 carbon atoms, a divalent silyl group having 2 to 20 carbon atoms,
`
`a substituted or unsubstituted, divalent aromatic hydrocarbon group
`
`having a ring formed of 6 to 24 carbon atoms, or a substituted or
`
`unsubstituted, divalent aromatic heterocyclic group which has a
`
`ring formed of 3 to 24 atoms and which is linked with Ar3 through
`
`a carbon-carbon bond, when n represents 3, L3 represents a trivalent
`
`alkane having 1 to 20 carbon atoms, a substituted or unsubstituted,
`
`18
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000018
`
`
`
`trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms,
`
`a trivalent silyl group having 1 to 20 carbon atoms, a substituted
`
`or unsubstituted, trivalent aromatic hydrocarbon group having a
`
`ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted,
`
`trivalent aromatic heterocyclic group which has a ring formed of
`
`3 to 24 atoms and which is linked with Ar3 through a carbon-carbon
`
`bond, or when n represents 4, L3 represents a tetravalent alkane
`
`having 1 to 20 carbon atoms, a substituted or unsubstituted,
`
`tetravalent cycloalkane having a. ring formed of 3 to 20 carbon atoms,
`
`a silicon atom, a substituted or unsubstituted, tetravalent aromatic
`
`hydrocarbon group having a ring formed of 6 to 24 carbon atoms,
`
`or a substituted or unsubstituted, tetravalent aromatic heterocyclic
`
`group which has a ring formed of 3 to 24 atoms and which is linked
`
`with Ar3 through a carbon-carbon bond, provided that , when both X1
`
`and X2 represent CR2R3, o and p each represent 0, q represents 1,
`
`and both Li and L3 represent substituted or unsubstituted, monovalent,
`
`divalent, trivalent, or tetravalent aromatic hydrocarbon groups
`
`each having a ring formed of 6 to 24 carbon atoms, or when both
`
`Xi and X3 represent CR2R3 , p and q each represent 0, o represents
`
`1, and both Li and L3 represent substituted or unsubstituted,
`
`monovalent, divalent, trivalent, or tetravalent aromatic
`
`hydrocarbon groups each having a ring formed of 6 to 24 carbon atoms,
`
`a case where Li and L3 are simultaneously linked at para positions
`
`with respect to Are is excluded.
`
`19
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000019
`
`
`
`In the formulae (1) and (2) , Al represents a hydrogen atom,
`
`a substituted or unsubstituted cycloalkyl group having a ring formed
`
`of 3 to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms,
`
`a substituted or unsubstituted aromatic hydrocarbon group having
`
`a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted
`
`aromatic heterocyclic group which has a ring formed of 3 to 24 atoms
`
`and which is linked with L1 through a carbon-carbon bond, provided
`
`that, when L1 represents an alkyl or alkylene group having 1 to 20
`
`carbon atoms, a case where Al_ represents a hydrogen atom is excluded.
`
`In the formula (1) , A2 represents a hydrogen atom, a substituted
`
`or unsubstituted cycloalkyl group having a ring formed of 3 to 20
`
`carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted
`
`or unsubstituted aromatic hydrocarbon group having a ring formed
`
`of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic
`
`heterocyclic group which has a ring formed of 3 to 24 atoms and
`
`which is linked with L2 through a carbon-carbon bond, provided that,
`
`when L2 represents an alkyl or alkylene group having 1 to 20 carbon
`
`atoms, a case where A2 represents a hydrogen atom is excluded, and,
`
`when X1 and X2 each represent 0, S, or CR2R3 , o and p each represent
`
`0, q represents 1, and both L1 and L2 represent single bonds, or
`
`when both Xi and X3 each represent 0, S, or CR2R3 , p and q each represent
`
`0, o represents 1, and both L1 and L2 represent single bonds, a case
`
`where Al and A2 simultaneously represent hydrogen atoms is excluded.
`
`In the formulae (1) and (2) , A1, A2, L1, L2 i and L3 are each
`
`20
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000020
`
`
`
`free of any carbonyl group.
`
`[00181 (cid:9)
`
`A case where the formula (1) has a structure represented
`
`by the following general formula (3) is excluded,
`
`\C
`
`Y3
`
`( 3 )
`
`provided that, X1, X2, A1, A2, L1, and L2 in the formula (3)
`
`has the same meaning X1, X2 , A1, A2, L1, and L2 in the formula (1) ,
`
`respectively.
`
`In the formula (3) , Y1, Y2, and Y3 each represent an alkyl group
`
`having 1 to 20 carbon atoms , a substituted or unsubstituted cycloalkyl
`
`group having a ring formed of 3 to 20 carbon atoms, an alkoxy group
`
`having 1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon
`
`atoms, a silyl group having 3 to 20 carbon atoms, a substituted
`
`or unsubstituted aromatic hydrocarbon group having a ring formed
`
`of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic
`
`heterocyclic group which has a ring formed of 3 to 24 atoms and
`
`which is linked with a benzene ring a, b, or c through a carbon-carbon
`
`bond, the number of each of Y1 and Y3 is 0 , 1, 2, or 3, and the number
`
`of Y2 is 0, 1, or 2.
`
`[0019] (cid:9)
`
`A case where the formula (2) has a structure represented
`
`by the following general formula (4) is excluded,
`
`21
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000021
`
`
`
`_ (cid:9)
`
`xi (cid:9)
`
`(4)
`
`I-3
`
`_ n
`
`provided that, X1, X2, A1, L1, L3 , and n in the formula (4)
`
`has the same meaning X1, X2, A1, L1, L3 , and n in the formula (2) ,
`
`respectively.
`
`In the formula (4) , Y1, Y2 , and Y3 each represent an alkyl group
`
`having Ito 20 carbon atoms, a substituted or unsubstituted cycloalkyl
`
`group having a ring formed of 3 to 20 carbon atoms, an alkoxy group
`
`having 1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon
`
`atoms, a silyl group having 3 to 20 carbon atoms, a substituted
`
`or unsubstituted aromatic hydrocarbon group having a ring formed
`
`of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic
`
`heterocyclic group which has a ring formed of 3 to 24 atoms and
`
`which is linked with a benzene ring a, b, or e through a carbon-carbon
`
`bond, the number of each of Y1 and Y3 is 0 , 1, 2, or 3, and the number
`
`of Y2 is 0, 1, or 2.
`
`When the benzene ring a is substituted by multiple Yis, the
`
`benzene ring b is substituted by multiple Yes, or the benzene ring
`
`c is substituted by multiple Y3s in the formulae (3) and (4) , each
`
`of the rings is represented as shown below.
`
`22
`
`DUK SAN NEOLUX
`EXHIBIT 1006
`PAGE 000022
`
`
`
`Aa) Aa/
`Y1
`
`Yl
`
`Y3
`
`r1=\
`
` Y3
`
`V3
`
`Y3
`
`[0020] (cid:9)
`
`The material for an organic EL device represented by
`
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