due brovets TT
`
`RopapSisebas
`Patentamt
`European
`Patent Office
`Oise sonapdass
`
` Steoremenes
`
`(14)
`
`EP 2 034 538 A1
`
`EUROPEAN PATENT APPLICATION
`published in accordance with Art. 153(4) EPC
`
`(43) Date of cublication:
`12.03.2009 Bulletin 2008/11
`
`(21) Application number OF7443408
`
`(22) Date of fing: 29.05.2007
`
`(51)
`
`Int ci:
`HOTL SiBaesen
`COTF Zig Bees.an
`COTE 7790 FEO}
`
`COOKpias 20e.od
`Our Zag eece.a}
`
`{86} International apctication number.
`PCTAP2ZO007A60921
`
`{87} fmernational publication number:
`WO 2007142088 (19.12.2007 Gazette 2007750)
`
`(84) Designated Contracting States:
`AT BE BG CH CY Cz DE DK EE ES FIFR GB GR
`HUE IS IT LILT LU LY MC MT NE PL PT ROSE
`SISK TA
`Designated Extension States:
`AL BA HR MK RG
`
`* MATSUURA, Masahicde
`Sodegaura-shi, Chiba 299-0293 (JP)
`* NAKANO, Yuki
`Sodegaura-shi, Chiba 298-0293 (JF}
`* IKEDA, Hidetsugqu
`Sodeqgaure-shi, Chiba 299-0293 (JP}
`
`(30) Prierity: 02.06.2006 JP 2000154205
`
`(71) Applicant idemitsu Kosan Ce., Ltd.
`Chiyoda-ku
`Tokye 100-8321 {JP}
`
`74} Representative: Gille Hrabal Struck Neidlein Prop
`Fioos
`Patentanweélte
`Brucknerstrasse 20
`
`40593 Diisseliort (DE)
`
`(78) inventors:
`+ IWAKUMA, Toshihire
`Sodeqaura-shi, Chiba 299-0293 (JP}
`
`
`(545 MATERIAL FOR ORGANIC ELECTROLUMINESCENCE ELEMENT, AND ORGANIC
`ELECTROLUMINESCENCE ELEMENT USING THE MATERIAL
`
`An organic electroluminescancedevice cam
`(S73
`prising a compound having a specific structure haying a
`heteroatom and an organic electroluminescence device
`which cornprises a cathode, an anode and an organic
`thin fiir: layer which comprises at leael one layer corm-
`prising at least a fight emitting leyer and is dispased be-
`
`tween the cathode and the anode, wherein at fest ane
`layer in the arganic thin film layer comprises the above
`compound, The device provides excellent efficiency of
`font emission, farma no defects in pkals, exhibite excel
`tent hest resistance and hae along We.
`
`EP2034538At
`
`
`
`Piinked Gy Jouve, FROFASS LER}
`
`

`

`EP2 034 538 At
`
`Deseriptien
`
`TECHNICA,
`
`{@6071] The prasent Invention caiates to a material for organic electraturninescence devices and an organic alectrota-
`minescence device using the material and, more particulary, to an organic electroturinescence device providing ex-
`celent efficiency of fight emission, forming no defects In pixels, exhibiting excellant haat resistance and having a feng
`life and a material for organic alectroluminescence devices which enables to obtain the devices.
`
`te
`
`BACKGROUND ART
`
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`{G002] An organic slectroluminescence (hereinafter, “electraiuminescence™ wil be relerred to as "EL", occasionally}
`device is a spontaneous light emitting device which ures the principle that a fuormscenl substance arnits ight by
`energy of racombination of hates injected from an anode and electrons injected from | cathode when an electric fleld is
`appiied. Since an orgemic EL device of the laminate type driven under a low electric voltage was reported by ©. W. Tang
`et ai. of Gasiman Kodak Company (©. W. Tang and S. A. Vanstyee, Applied Physics Letters, Volume $1, Pages 913,
`1387}, many studies have bean conducted on organic EL devices using organic materials aa the conatinting materiais,
`Yang et al. used risth-nydrogyquinalinolatojaluminurmfor the lignt emitting layer and a triphenyidiamine derivaive for
`the hole transporting layer. Advantages of the lerninate stricture are that ine efficiency of hole injection into fhe light
`emitting layer can be increased, that the efficiency of farming excited particles which are formed by blocking and recanr
`bining electrons injected from ihe caihode can be increased, and that exciied pafiicies formed within the Nght erniiting
`fayar can be encfosed. As the structure af the organic EL deviog, @ two-layered structure hevitg a hole transporting
`iinfeating) Jeger and an electron transporting and light emitting layer and & three-layered sbucture having a hole trans:
`porting Onjecting} layer, a ight emitting Jayer and an electrontransporting (injecting) layer are well known, To increase
`the efiiciency of recombinedion of injected holes and electrons in the devices of the laminate type. the structure of the
`devices and the process for farning the device have been studied,
`fQ003] As the light emitting material, chelate complexes such as iis(B-quinoinolaio}aluaninun complex, cournradn
`derivatives, ielraphenyinutadiane derivatives, distyrylaryiene derivatives and oxadiazole derivetives are known. It is
`reported thet light in the visitie region raoging frorn blue light ta red light oan Ge obtained by using these light emitting
`materials, and deveionment of a device exhibiting color images is expected (for examole, referto Patent Refereroes 4
`to 3}.
`tis recently proposed that an organic phosphorescent material other than the Huorescent matedal is usad In the fight
`ermtting layer of an organic EL device dor example, refer to Non-Patent Meferance } and Non-Patent Ralerance 2). As
`described above, a greet efficiency of ight aniissianis achieved by utizing an organic phosphorescent material excited
`to the singlet state and the trnlet state in ihe fight emitting layer of an erqanic EL deviog. it is considered fhat singlet
`excimers and triplet excimers sre formed in relative amounts of 1:3 due to the difference in the multinlicttyof apin when
`etectons and holes are racornbined in an organic EL device. Therefore, iis expected thal an efficiancy of ight emission
`Bio ad times as great as that of a device utilizing THuorescence alone can be achieved by uthizing a material emitting
`phosphorescent fight.
`f4004]
`In the organic EL devices described shove, a consiruntion formed by successively larninating layers such as
`an anode, a hole transporting jayer, an organic ight emitting laver, an electron transporting layer fa hole barrier layer),
`an electron tranaporting layer and a cathode is used eo thal the excited state of the tfplet or excimers of the trolet de
`not fai to ernit
`ight, emda host compound and a phosphorescent compound are used far the organic fight emitting layer
`
`ifor example, Patent References 4 to 8).
`In these patent references, host materiais having a skeleton structure of
`dibenzaturan or dinenzevihlaphene are described. However, fis not described whelher = device using the above host
`material exhibits more excellent performance than devices using other materiais having the carhezolyl skeleton structure.
`wo descriptions can be fouron combinations having silcon atom or qarnanium atom, aither.
`iq Patent Reference 9 and 10, comoounds having substituents such as aryisilyl groups are described, Mowever, the
`compounds dascribed in the present invention are mot described. Moreover, no descriptions are found on the useful
`effect as the material for organic EL devices, in particular, as the phosphorescent material for organic EL devices ernitting
`bluish §ght, such as the efact that the energy gao af the triplet stake can be keot oread.
`in Patent Reterence 11 to 18, aryisiane-based compounds and aryiqermane-basad compounds are described, and the
`use of these compounds as the host material for a phoschorescent device emitting Gluish ight ig described in the
`exvampies, Hawever, the compounds dascrited in ihe present invention are not described, and the effects of the com-
`pounds are mot known.
`[e005]
`
`fPatent Aeference 1} Jasanese Patent Application Laid-Open No. Helse! 6(1996)-239555
`
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`EP2 034 538 At
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`[Patent Asferance 2] Japanese Patent Appiication Laid-Open Ne. Helies! 7{1985)-1 38561
`iPatent Asference 3} Japanese Patent Appication Laid-Open No. Helse! (7991 )-200889
`[Patent Reference 4] international Patent Application Laid-Open Ne, WOO O1STeS
`[Patent Reference 5] Japanese Patent Application Laid-Open No. Helse! §(1803)-1 69485
`[Patent Reference 6} Jaganese Patent Application Laid-Open Na. 2004-00235 1
`[Patent Reference 7] intermaetiona! Patent Apolication Laid-Qnen No. WOod/og8845
`{Patent Reference 6] Japanese Patent Apolcation Laid-Open No. 2002-Q08837
`iPatent Aafsrence Si Japanese Patent Application Laid-Open Ne. 2003-138251
`[Patent Reference 10] Japanese Patent Application Laid-Open Ne. 2000-0573966
`fFatent Reference 11] Intermational Petent Apoioation Laid -Ooen No. WooOd/086598
`[Patent Raference 12] United States Patent No, 2004-2097 15
`[Patent Reference 13] Japanese Patent Application Laid-Open Ne. 2004-19463
`[Patent Reference 14] Jananese Patent Application Laid-Gper Na. 2d08-1859303
`[Patent Aaference 15] Japanese Patent Application Laid-~Gpen No. 2005-34 7276
`[Patent Reference 14] Japanese Fatent Applicetion Laid-Open No. 2004200104
`fPatent Reference 17] Japanese Patent Application Laid-Open No. 2o08-3 10872
`[Patent Asferance 128] Japanese Patent Application Laid-Open No. 2006-g08884
`INon-Patent Relerance 1]. F. O'aiien and M4. A. Balto etal. “improved energy transfering electrophoaghorascant
`devices" Apnited Shysics fetters Vat. 7.4 No. 3, po 442-444, January 18, 1899
`{[Noen-Patent Reference 2] M.A, Baldo at al. Very high-efficiency gr@en organic light-emitting devices based on
`etectraphosahorescence™ Applied Fhysice laters Val. 7B No.1, oo 4-8, July &, 1392
`
`DISCLOSURE OF THE INVENTION
`
`{Prablams to be Overcame by the Invention]
`
`{Q006] The resent invention has Geen made ip overcome the above problems and has an object of providing an
`organic EL device providing excelent efficiency of light emiesion, fonning ne defects in pixels, axhibiting excellant haat
`resistance and having 2 long Rie and a material for organic EL devices which enables to obtain the device.
`
`[Means for Overcoming the Prablerns}
`
`{[Q007] As the result of intensive studies by the present invertors, if was found thal an orgariic EL. device providing
`excellent efficteacy of ight emission, forming no defacts in plvels, exhibiting excellent heal resistance and having a long
`fe could bo obtained by using a compound moresented by the following general formula (1) or (¢} as the material for
`the organic EL device. The present invention has been campleted based on the knowledge.
`The praesent Invention oroviies a mmatectal for organic EL. devices which camprises a cornpaund represented by the
`following general fanmuta (1) or {2}.
`As the first aapect, the present invention provides a material for organic EL devices which comprises a compound
`represented by ite foflawing general formula (1):
`[6008]
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`{8009} wherein A, io Ay each iIndependenily represent hydrogen stom, @ halogen atom, an alkyl group having t to 40
`carbon atomswhich may have sunstitvents, 4 heterocyclic group having Sto 20 carbon atoms which may have substit-
`uents. an alkoxy) group having } fo 40 carbon atems which may have substituents, a narecandensed ant grouhaving
`8 to 40 carbon atoms which may heave substituents, a condensed aryl group having 6 to 12 carbon atorns which may
`have substiuents, an aryloxyl group having 6 to 20 carbon atoms which may have substituents, an eraiin’ croup having
`
`

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`EP2 034 538 At
`
`7 to 20 carbon atome which may have substituents, an alkeny! qrauc having 2 to 40 carson atoms which ray have
`substituents, an alkyiamino grows having | to 40 carbon atoma which may nave substituents, an aralkylamine croup
`having ?¢ to 60 carbon atoms which may Nave substituents, an alxyteilyl group naving 3 to 20 cevbon atoms which may
`have subeituents, an arylsiy! group having 8 to 40 carbon atoms which may have substituents, an aralkyisily] group
`having & te 46 carbon atoms which may have substituents, an alilgermarnium group having S te 20 carton atoms which
`may have subsituents, an anigermanium group having 6 to 40 carbon atems which may have subsaltuents, an ar-
`atkylgermanium graug having 8 to 40 carver atoms which may have substituents, a khetoand grou having 7 to 40 carbon
`atoms which may have substituents, a halogenated alkyl group having 1 to dO carbon atoma which may have auosthuants,
`CYENG group of @ structure represented by following general fannuls (a), and at least one of FR, to A, has & atructure
`represanied oy General fonmuta {ak
`{O070]
`
`"s3
`
`om
`
`awe
`
`in general jonnula (a), L representing & single bond, an alkylene group having ft te To carbon ateme which may
`{OG17}
`have substituents, a non-candensed arylene group having 6 to 40 carbon ators which may have subsituents, a con-
`sensed arlene group having 6 to 12 carbon aioms which may have substituents ar a divalent aromatic heterocyclic:
`group having 3 fo 40 carben ators which may have substituents, Y, to ‘f. each independently represeriting an alky!
`oroup having t te 710 carrion ators which mayhave substituents, an aryl group having 6 to 20 carbon atoms which may
`have substituents or an aromatic heterocyclic group heaving 6 to 32 carbon atoms which may have substituents, and Z
`representing silicon atom or gerrnanium atom, and
`Xyepresents sulfur atom, oxygen atom, a substituted siicon atom represented by SIR, A, or a substituted germanium
`
`atom represented by GeFAy, By, R,, A, and A, each indeoendently representing an alkyl group having | to 40 carben
`atorns which may have substhivvents or an ary! qroup having 6 to 26 carben atams which may have subsituants.
`[0042] As the second aspect, the present invention provides a qiaterial for organic EL devices which carmprises a
`cormpound represented by tne following general formula (2):
`
`‘
`
`f Ripe Ray
`
`[RZ os \
`So oie zy }
`RO ‘An
`
`4-7
`
`
`
`
`an alkyl group having
`{O013} wherein Ry, to A, and Reach independently ranpresant hycimngen atom, a halagen atom,
`} to 40 carbon atorns which may heve substituents, a helerocyotic group having 3 te 20 carbon alome which may have
`subsfituents, an alkoxyl qroup having 1 to 40 carbon atorns which may have substituents, a non-condensed ary! group
`having 6 fo 40 carbon atamse which may hawe substituents, a condensed aryl group having 6 fo 12 carbon atoms which
`may have substituents, an arykowyl group having 6 io 20 carbon aforns which may have substiiuents, an anatkyl group
`having ¥ to 20 carbon atoms which may have substituents, an alkenyl! group having 2 to 40 carbon atame which may
`neve subsiuents, an alkylamino group having | to 40 carbon atonis which mayhave substituents, an araikylamine
`group having 7 to 60 carbon ateme which may have substituents, an alkylstyl group haying 3 te 20 carbon atoms which
`may have substituents, an ecyishyl group paving & to dO carbon stome which may nave substituents, an aralkyisiy! group
`having 8 to 40 carbon atoms which may have subsituents, an alkyloennanium group having 3 to 20 cargon atems which
`may Rave substituents, an anigermanium group having & to 40 carkon atoms which may have substituents, an ar-
`alkyigermaniur group heving 8 fo 40 carbon atoms which may have substituents, a ketoary! group having 7 to 40 carbon
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`EP2 034 538 At
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`atoms which may have subetituants, a halogenated alky! qraup having | fo 40 carhon ateme which may have substitients
`oF Cyan group,
`xX, Land 2 are as defined in general formula (1), ¥ is ae defined for Y, to ¥., in qanerel fornula (1), and 4 represents an
`heger at } te 4.
`
`{@074] The present invention also provides an organic alectroluminesceance davice which cornarises a cathade, an
`anode and an organic thin fim layer which comprises at least one layer comprising at leaat a Hight erniftiing fayer ard is
`disoased behween the cathode and the anode, whernsin at least one layer in the orgenie thin filn layer cornprises the
`material for ordaric elactroluminescence davices descrined above.
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`THE AFFECT OF THS INVENTION
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`{G035] An organic EL device oroviding excellant aiiciency of light emission, forming no defects in pixels, exhioiting
`excellant heal rasisiance and having @long ite cart be obtelned when the material for organic ELdevicas comprising
`the compound represented by general farmula (1) or (2} is usact
`
`THE MOST PREFERRED EMBODIMENT TO CARRYOUT THE INVENTION
`
`{8036] The present invention orovides a materia! for organic EL davies comprising a compound represented by the
`following general formula {Tt} ar (2).
`The compound reoresented by general fennula (1) will be described In Ine feliawing.
`in general formula (1), A, to A, each independently represent hydrogen atom, a halogen atom, an alkyl group having
`{to 40 carbon atoms which may have suustiuents, a hetarocyolin group havin SG to 20 carben atoms which may heve
`substituents, ar ekoxyt group having { io 40 cerbor aterne which may have substituents, a narroondensed ary! group
`having 6 to 40 carbon atoms which may have subsiltuecta, a condensed aryl genup having Bie 12 carbon atoms which
`may have substituents. an aryloxy! group hevirng 6 te 20 carbon atoms which may have suestituents. an aralkyl group
`having 7 fo 20 carton atome which may have substituents, an alkenyt group having 2 to 40 carbon atorns which may
`have substituents, an alkylamino group having { to 40 carton aloms which ray have substituents, an aralkwiamino
`group having 7 to 60 carbon atoms which may have substituents, an alkyisiy! group Naving 3 to 20 carbon atoms which
`may have subattuents, an aryishyl groun having & te 40 carbon atoms which may Nave substents, an araikyisiy! group
`having & to 46 carbon
`atoms which may have substituents, an alkyigernanium group having 3to 20 carbon atame which
`
`may have subaiivuerds, an aryigermanium group haying 8 to 40 carbon stems which may have subsituerts, an ar-
`alkylgernnanium orcas having 8 to 40 carbon atoms which may have subsiiuects, a ketoaryl group having 7 to 40 carton
`ators which may have substiivents, 4 halogenated alkyl group having 1 to 40 carbon atoma which may Nave suosthuants,
`CYENG group or @ structure regresented by fafowing general farnula (2), and et least one of A, to Ay has a structure
`represanied oy general formula (ed.
`{Q0T7] Examples of the halogen atom inclucte fluering, chlorine, bromine and iodine.
`Exanmes of the aikyl group include methy! group, ethyl group, prapyl group, isoprepy! qreup, n-burd group, s-buné
`group, isobubyd group, tboutyl greug, n-nenty! group, n-hesyl graup, n-hepty! qroup, n-coty! gqroun, n-nonyl group, a-dacyi
`group, reundecy! group, n-dodecy! group, n-tridecy! group. n-tetradacyl group, n-pentadecy! group, n-hesadeayl group,
`n-heptadeoy! group, n-ootadenyt groun, neopentyl group,
`t-mnethyloentyl group, a-methylpenty! group. 1-pentylhexy
`group, T-butyiventy! group, T-heptdoctyl group, S-methyjpenty] graup, hydroxymethy! group, T-hydeoxyethy! group, 2-
`hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1o-dihydraxyleopropyl croup, 2. 3-dihydrooy-t-
`butyl group, 1.2,3-trhydroxyprory! group, chloromethyl group, |-chloroethyl group, &-chioroethy! qrous, 2-chiorolscbuty
`group. 1.2-dichioresthy! group, 1,S-dichloroisepropyl group, 2,3-dichioro-t-butyi group, 1.2,3-trichloroprooy! group, ore-
`rmomethyl group, j-bromeoethy! group, 2-bromoethyl group, 2-bramoisebury! group, 1,2-dibramoethy group, 1 3-dibro-
`moaoisapropy! croug, &,4-dibrorno-t-butyi group, 3,2,S-tritramepropyl groun, lodeme#thy! group, t-lodoethy! graup, 2-ia-
`doetipd aroun, Aiodalasbuty! group, 1.2-diioceathyl group, 1,9-dlodsiseproanyl group, 2,4-dieda-t-hufyt group, 1,2,3-
`tHiodoprapyt graun, arinomelty! group, t-arminaethy! group. 2-aminoethyl group, 2-aminolecbuty! group, 1 .2-diarainae-
`thyl group, 13-diarningisopropy! grous, 2.3-dlamino-t-buty] grows, 1.2.3-thaminoarenyl graup, cyanomethyl group, 1-
`cyanoethyl grouse, 2-cyanoeihy! group, 2-cyanosobuly! group, t2-dicyancethy! groun, |a-dicyangisopropyl group, 2,5-
`dicyane-t-bubd group, 1.2.3-neyanopcopy! group, nitramethyl croup, }-nitresthyl group, ¢-nitroeihy! group, 2-nitraisobuty!
`group, 1 2A-dintroeiny! group, 1 ,3-diniirotsapropyt qroup, 2.3-dinitre-t-outy! group, 1 .<.4-tnnitrapropy! group, cyciopanns
`group. oyciohexy! group, cycinecty! group, 3 S-tetramethyloyciohexyl group.
`fO0TS] Among thase alky! groups, methy! group, afhy! group. propyl! group, Isopropyl group, n-butyl grows, s-nuty
`group, isobutyl group, toutyl group, n-oentyl group, n-haagl group, n-heptyl croup, m-octy! groups, n-nonyl group, n-decy
`group, p-undecy! group, a-cdocdecyl group, n-fidecy) graup, n-betradecy! qroun, p-geniadacy! groun, c-hexadecyt group,
`n-hepiadacyl group, n-ociadecy) group, neopenty! group, T-methylpentyl grouc, | -pentdhexyi! graug, t-butypenihygroup,
`i-heptyloctyl qroun, cyclohexyl groun, oyclooctyl group, 3.5-tetramethyleycicheay! group are preferable.
`
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`EP2 034 538 At
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`-oyridiny! orous, T-imidazold croup, 2-imidazolyl group, T-pyrazoiyl group, T-Indaliiny! qroup, 2-indolidiny! group, 3
`
`fxarnpies offhe heherscyctic group inchude T-oyrroly! greup, 2-pyrrolyl group, S-cyrrohd group, pyraziny groun,
`pa9}
`indticiny group, S-indolidiny! group, Gindaliciny! group, 7-indolidinyl group, S-dndetidiny! group, 2-imidazopyrdiny!
`group, S-imdazapyrdinys group, 5-inidazooyridiazy! group, 8-imidazonyndinyl group, 7“rnidazopyridiny! graun, B-imi-
`darooyidiny! group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyt group, 2-indolyl group, 3-Indaly! group, 4-indolyi group,
`S-indoly! group, G-indoyy! group, F-indoly! group, T-acindolyl qraun, 2-iscindaty! group, 3-iscindaly! group, 4-isoindoly!
`group, Siscindolyl group, G-iscindalyl group, 7-soindelyl croup, 2-fury? grome, G-fury group, e-benzofucaoy! group, 3+
`benzofurany! group, 4-bengzofurany! group, S-benzofurany! groom, 6-benzeofurany! group, 7-pengeturany! group, t-iao-
`benzafurany! group, S-incbenzofurany! graug, 4isobenzoafuranyl groug. S-isobenzalurany! grous, G-isobanzofunany!
`group, 7 dsabenzaturany! groups, 2-quinolgroup, 3-quinoll group, 4-quinelyd group, S-quinaly aroup, G-ouinaly group,
`*-quinoly! group, B-quinoly! group, I-isoduinolyl group, G-isequinoly! group, 4-isoquinely! group, S-lscquinaly! group, 6-
`isoquinoly! groun, F4saquinals group, 8-isoquinolyl group, 2-quirroxanyl group, S-quinoxanyl group, G-quinoxany greup,
`j-catagzolyl group, 2-oarbazoly! group, S-earbazoly! groans, 4-carbazolyl group, S-carcazcht group, Becarbalin-T-yt, 6
`carmdin-G-y, Becarbotin--yi, P-carbolin-So4, f-carbolin-i-yi, B-carbolin-7-yl, B-carbolin-6-y1, B-carbolin-g-yi, f-nhen-
`anihdoiny! graug, 2-phenanthrisiny! groug, Gqchenanthriding! group, 4-phenanthridiny! group, 6-phananihndiny group,
`7-phenanthvidinyl group, S-phenanthridinyl group, 9-phenanthidiny group, TO-ghenanthydinyl group, t-acridiny! group,
`eacrdinyl group, S-aoddiny! group, ¢-acridiny! group, 2-acridinyd group, 1.7-phenanthrolin-244 group, 7 /phenanthralire
`
`.Y group, 1,/-phenanthrolin-4-yi grove, 1.7-phenanihrotin-6-yl group, 1,7-phenanthralin-6-" group, 1,?-phenanthrotin-
`oo group, 3S-phenanthrolin--yi group, 1,4-phenanthrolir-S-y1 group, 1,8-phenanthrolin-O-yi group, 7,aohenanthrolin
`
`-yi group, 1,7-chenanthralin-9-yl group, 1,7-phenanthrelin- 10-41 droaup, 1,8-thenanthyrolin-2-y1 group, 1,8-phenanthrelin-
`
`7-Yi group, 1,é-phenanthrolin-G-yl group, 1,8-phenanthrolin- 1 O-W croup, 1, 3-phenanthroin-2-yi group, 7,6-phenanthrotin-
`Beya-yl group, 1,S-phenanthrotin-a-yi group. 1,S4phenanthroiin-3-y group, 1.S-phenanthrotin-6-"1 group, 1,2-phenanthratn-
`ry group, 1O-vhenanthrolin-84 group, 1,8-pheaaniirolin-1O-yi group, 1,1O-chenanthrelin2-y! group, 1,7O-gchenan-
`throlin-3-yi graug, 1, 1¢-phenanthrolin-4-yi group, 1, 1G-pnenanthrofin-&-yl group, 2,.3-phenanihrotin-t -yi group, 2, 9-ohen-
`anthroiin-3-y1 group, 2.a-phenanthrolin-4-yi greup, 2. d-phenanihrotin-&-yl group, 2, 9-phenanihrolin-8-y1 group, 2, 9-ohen-
`
`anthyalin-7-¥! group, 2,5-ohenanthrotin--yi group, 2,8-phenanthroiin-10-y) group, 2,8-prenenwoul grauo, 2,3-
`phenenthrotin-Si group, &2,8-phenantiralin.4-yl group, 2.8-phenantirolin-S-yi group, 28 -pheaanthralin-G-y group, ¢,8-
`phenanthrotin-7-yi group, 2,8-‘phenanthrefin-Syi croup, 2,8-phenanthrolin-10-yi group, 2,?-phenanthratin-ty group,
`
`2,7SNENentired-3-vi group, 2, /-phenanthrolnd-yi group, 2.7-phenanthroln-5-yi group, 2 7-phenanthralin-8-8 graup,
`2,7-ohenanthrot:-8-yl group, 2, F-phananthratin-S-yl group, 2, 7-chenanthrolin-iO-yi group, t-phenaziny! group, 2-ohen-
`aziny! grave, T-ohenagihlazinyt grove, 2-ahenathiaziay! qroug, Q-phenothiasiy! group, 4-phenothiazing! group, 1¢-ghe-
`nothiaginy! grap, i-phencxaziny! group, 2-phenoxaziny! group, S-phenoxaginy! group, 4-phenoxaziny! group, 1G-phe-
`noxaginy! group, Z-oxazoly! group. d-oxazoly] group, S-oxazolyl group, 2-oxadiagell group, S-oxadiazoly! grown, 3-
`hurazany! group, 2-thienyl grouo, S-thieny! group, 2-rnethyloyrrob tad group, 2-methylpyrrol-3-y! group, 2-methylpyrral-
`4-41 group, f-methylpyrral-6-y! group, S-rnethyloyral- fyi Group, S-methyl- oyrrat-2-y4 group, S-methyipyrrol-4-yi group,
`Semethyipyrol-S-yl group, 2-t-butyipyrreld-y1 group, 3-(2-phenylpropyijpyrral-] -yi group, 2-methyl t-indokd group, 4-
`
`metnyh t-indaly! group, 2-methy!-3-indaly! grauo, 4-merhyl-d-indesd group, #4-butyl t-indohyl group, 4-bbutyh t-indolyi
`group, 2-t-butyl-3-Indely! arougs, 4-t-bityG-indaly! group, i-dibenzofurany! grous, 2hbenzefurany! groug, S-dibenzre-
`furanyl group, 4-dibenzoturany! group, 1-didengoitiogheny! group, 2-disenzcthiophery! group, 3-dibengothiosheany!
`oroup, 4-dibenzathiophenygroup, t-silavhuoreny! group, 2-sdafiuarenyl group, G-siefluereny! geoup, 4-silafuorany] group,
`i-germatiuorenyl group, 2-germafiioreny! group, 3-germaflucrenyl group and 4-germafluorenyl qroup.
`(9020) Amang these heterooyvalic groups, 2-oyridinyl group, t-Indolidiny! group, 2-ineolidiny! group, 2-Indolidingl group,
`&-Indolidiny! group, 6-indoliding’ group, 7-indolidinyl group, 8-Indaliciny! group, 2-imidazonyridiny! group, 3-“iesdazopy.
`ridiny! group, &-imidazopyridiny! group, 6-imidazopyridiny! group, 7-imidazopyridiny! group, B-imidazopynadinyl group, 2
`pyridinyt group, 4-oyridiny! group, T-Indalyt group, 2-Indolyl group, 3-indoiyi group, 4Indely! group, S-indaly! group, 6-
`indohyt! group, 7-incioly! group, t-iseimdolyt groug, Sieoindaly! group, Gissindotyl group, 4-Iscindohd groun, 5-iscindoly!
`group. Giscindalyl croup, Y-iscindoty! group, t-cerbazol! group, 2-carbazoly! group, S-carhazohd graug, 4carbazaly!
`group, Scearbagohd group, }-dibenzofurany! group, 2-cloenzofunany! group, G-cibenzofurang group. 4-oibenzofurary
`group, t-dibenzothiophenyl groun, 2-dibanzethiopheny group. 3-oisenzothionheny croup, 4-dibenzothioshenygroup,
`i-siadivoreny! croup, 2-ailafivoranyl group, S-sdaflucrenyt group, 4-silafluoreny! group, T-qermafiuereny! group, 2-ger
`mafiuereny! group, 3-gernaficerenyl grouo and 4-germalluoreny! group are oreferable.
`fOG21}
`The alkoxy! group is a8 group representad by -OV. Examples of the qraup represented by ¥ include the groups
`
`described above as the ees of the alkyl group, and preferable examples of the group represented hy Y inchide
`
`the groups described a3 the preferable examples of the alky! groun.
`Examples of the non-condensed ary group include phenyl qroup, 2-biphenyly! gqroun, S-hiphenyiyl grous, 4-biphenyhyst
`group, p-lerohenyl¢-y] group, p-teroheny!3-yi group, p-tenohenye2-yl group, ri-terphenyl-4-y{ group, npetercheny)-O-yi
`group, m-Lerphanyl-2-y! groun, o-dalyl group, r-toly! group, p-toly] group, o-t-butyisheny! group, p-/2-chenylnrepyl}-cheny!
`group, 4-methylbiphenylyt group, 4"-t-butyi-pterohenyl-4-9l group, c-cumeny! group, m-cumenyl group, p-cumeny!
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`group, 2 Soci group, 3.4-ydyl group, 2.5-xylyi qraun, maesityl qraun and s-quarter-phenyl graun.
`Among these groups. ohany! group, 2-bishenyly! group, d-cishenytyl group, 4-biphenyhd group, mtesphenyl-4-vi group,
`niterphenyl-3-yi group, m-ferphonyl-e-yl grows, p-lehd group, 3,4-xylyl group and m-quarterphenyl-2-yl group are pref-
`erable.
`
`Exarnnies of the condansed ard group include Y-naphiny! grou and 2-naghihyl group.
`fene2} The aryioxy! group is & group represented by -QAr Examples of the group represented oy Arinclude the groups
`described above as the examples of the non-condensed aryl group. Prefemble examples of the group reprasentead by
`Af include the grouse described as the preferable exarioisa of the non-condensed ary! group.
`Exempdes of the aralky! craus include benzy! group, t-phenylethy! graup, 2-shenylethyl sroup, t-oahenyfilsonrepyl group,
`a-chenylisopropy! arcu, ohenyit-bulyi aroun, e-neghthymethy group,
`t-o-napsthyiethy! arous, 2-c-nachthylehy
`group, t~s-neohthylisocropy! droup, 2-c-naghinylisoprepyl group, B-naphihyimethy group, 1-f-nephthylethy! group, 2-
`p-enapnihyiethy group, 1-S-naphtnylsopropy! group, 2-f-naphthylisopropy! group, T-pyrrofytmelnyt group, 2-(l -pyrroyyh
`ethyl grouo, p-rnathyloenzyl group, memethybeneyl graug, o-methylbenzyl group, p-chicrabenzy!l group, m-chierabenzy!
`group, o-chicrobenzy! group, p-bromotenzyl group, n-bromobanzy! group, o-hramebenzyl group, p-lodoabenzyl group,
`in-lodobenzyl group, ododobenzyl group, p-hydroxybenzy! group, m-hydrosybenzyl group, o-hydroxybenzy! group, g-
`aminobenzyl group, m-aminobenzyl group, o-aminobenzy group, p-nitrobenzyl group, m-nitrobenzy! group, o-nRtrobenzyi
`group. p-oyanobenayl group, m-cyanobenzy! group, a-cyanabenzyl aroup, 1-hydroxy-<¢-phenyligoprapyl group and 1-
`ohlora-2-phenylisoorapy! grup.
`Among these aralkyl grouns, banzyl group, p-cyanobenzyl group, m-cyancbenzy! group, c-cyanobanzy! group, 1-phe-
`nylethy! crows, 2-pherylethyl group, i-phenylisepropy! grows and 2-phenylisonropy! groups are preferable,
`fQ023] Examples cf the alkenyl! group include vinyl group, allyl group, d-butenyi group, 2-butenyl croup, S-buteny!
`group, 1, 3-bitedieny! grou, T-methyiviny! group, styry! group, 2.2-diohenyiviny! group, t2-dichenyiviny! group, T--neth-
`ylaillyl group, 1, t-dimethydadiyt group, 2methylallyl group, t-chenytalld groua, 2-phenyladyt group, S-pheoylaliy! group,
`3,o-diphenylaily! group. 7.2-dimethylally! group, t-phenyl-t-outeny! group and S-phonyl-T-buteny! group, Among these
`groups, sivryl group, 2.2-diphenylvinyl group and 1,2-diphenylvinyl group are preferable.
`{0024} The alkviamine group andthe aradkylanino group having 7 to 60 carbon atoms whith ray have substituents
`are caprasemed by -NG,O,- examples of the groups represented by G, and Q., sach indanensently, inclucis the groups
`described above as ihe examplas of the alkyl group, the ary group and the araliyt group. Preferable examples of the
`groupe represented by G, and ity Indluge the groups described above as tne preferable examples of the alky! group,
`the aryl group and the aratkyt qroup.
`Exmrngles of the alkyisity group Include trimethylsilyl qraups, irieltyishyl group, ttutyinirnethyleilyl group, vieyidimethyisiy
`group and propyidimnetiylely! croup.
`Examples of the arylsdy) group include iiphernyisily! group, tribiphenylsiil group, ditepphenyiphenylisiy! group, phenyled-
`imeihyishy! group and t-butyidipnrenyisiyi group.
`Examples of the aratkyisilyt group include tribeazyisily! group, benzyldirnethytely! qroup and t-butylbengylaint group.
`{8025} Examples of the alkyigennanium groun include timeihy:-germanium group, tethyigermaniun group, t-bufyid-
`tmeihyigermnanium group, vinyidhnethyigenianium group and orepyidimethyigernvanium group.
`Examples of the aryigermanium graup include tiphenyigernanium group, tibiphenyligennarium group, diteyshenyiphe-
`nylgermaniungroup. pheoyldimethyligennanium group and Lbutyldighenydoernanium group.
`Eyeengdes of the snaikylgermanium group Include tribenzylgenmaniurn group, benzyidiynethyigennanivm group ared t-
`butyidibenzyligermanium group.
`The ketoans group is a group represented by -COAr,. Examines of the group represented by Ar, Include the groupe
`described above as the examples of the anf group. Preferable examples of the group represented by Ars inchide the
`groups described above as the oraterabie exarmplas of the aryl group.
`Examples of the halogenated alkyl qraup include tne alkyl groups described above wherein at least one hydrogen atom
`of the alky! group is substitted with at least one halogen aiom. Preferable cxampies of the halogenated alkyl group
`inciucia the alky! groups descrihed shove as the preferable exarmpies whersin at iaast one hydrogen atom of ihe alky!
`group is subseiituted with at least ane halogen abom.
`{0626}
`In general formula (1), X represents cufur ator, caygen atom, 6 substituted silicon slom represented by SIR_R,,
`oF @ substituted germanium atom rapresented by GeR.Ry Ry. A, R, and Ay each independently represent ar alkyl
`group having 1 to 40 carbon atoms which may neve substhuenis or an and omup having 6 te 20 carbon atorns which
`may have suvettuents.
`Examples of the alkyl group represenied by F.,. R,,, A, Rad Ry inchide the groups described above as the examples of
`the alkyl group represented by R, to Ry. Preferatie examples include methy! group, ethyl group, propyl group and butyl
`group
`Examples of the ary! group having & to 20 carbon atoms represented by R,. AL, 5, aad Ay include the groupe deserbes
`above as the exarnpies of t