有机电致发光
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Originalarticle
Synthesisandcharacterizationofcarbazole-baseddendrimers
asbipolarhostmaterialsforgreenphosphorescentorganiclight
emittingdiodes
TingZhanga,*,Dong-QingXub,Jun-MingChena,PingZhanga,Xu-ChunWanga
aSchoolofChemistryandMaterialEngineering,AnhuiScienceandTechnologyUniversity,Fengyang233100,ChinabCenterofAnalysisandMeasurement,AnhuiScienceandTechnologyUniversity,Fengyang233100,China
1.Introduction
Sincethereportoforganiclight-emittingdiodes(OLED)based
onphosphorescentemitters,therehasbeenintensiveinterestin
thesedevicesbecausetheycanharvestbothsingletandtriplet
excitonsforemission,providingtheopportunitytorealizeinternal
quantumefficiencycloseto100%[1].Untilnow,mostofthe
efficientphosphorescentorganiclight-emittingdiodes(PHOLEDs)
havebeenfabricatedthroughvacuumthermalevaporationwhich
allowsforcomplicatedverticaldevicearchitecturesanddelivers
excellentdeviceswithhighefficiencies[2,3],butrequires
complicatedtechnologicalprocessesand,consequently,ismuch
morecostly.Itisgenerallybelievedthatsolution-basedprocesses,
suchasspin-coatingorink-jetprinting,arerelativelyinexpensive
andcanbeutilizedforthepreparationoflarge-areadisplays[4].To
date,solution-processedPHOLEDsaremainlyfocusedonpoly-
mericmaterialsbyincorporationofheavymetalcomplexes
throughphysicalblendinginpolymerhostslikepolyvinylcarba-
zole(PVK)[5]andpolyfluorene(PFO)[6]orchemicalbondingon
polymerchains[7].However,theapplicabilityofpolymericmaterialsisgreatlyhamperedbyintrinsicdisadvantages,such
astheuncertainmolecularstructureanddifficultyinpurification,
whilethepurityofmaterialshasagreatinfluenceonelectrolumi-
nescenceperformance.Incontrast,conjugateddendrimershave
emergedasanewtypeoflight-emittingorganicmaterialsfor
applicationinOLEDs[8].Theycombinetheadvantagesofboth
smallmoleculesandpolymericmaterials,forexample,repeatable
monodispersityandhighlevelsofpurityofsmallmolecules,and
goodsolubilityandfilm-formationabilitybywetmethodsof
polymers[9,10].Therefore,dendriticmoleculeswithgood
solubilityandexcellentthermalstability,eitherashostsordoped
emittersforsolution-processiblephosphorescentlight-emitting
devices,havebeeninvestigated[11,12].
Duetotherelativelylongexcitedstatelifetimesoftriplet
emitters,theheavymetalcomplexesareusuallydopedintohost
materialstoreducetheself-quenchingandtriplet–tripletannihi-
lation[13].Bythecombinationofbothholeandelectron
transportingmoietiesinonemolecule,bipolarmoleculesinthe
questforhighlyefficientPHOLEDshavearousedconsiderable
interestbecausetheyenableabalanceddensityofchargeand
simplifieddevicestructures[14,15].Oneofthemostimportant
corestructuresofbipolarhostmoleculesisthecarbazolemoiety
duetoitslargetripletenergyandgoodhole-transportproperty
[16–21].Toachievebipolarityinthemoleculardesignsbased
onChineseChemicalLetters27(2016)441–446
ARTICLEINFO
Articlehistory:Received7July2015Receivedinrevisedform10September2015Accepted17December2015Availableonline6January2016
Keywords:OLEDsBipolarhostmaterialsDendrimerCarbazoleDibenzothiopheneABSTRACT
Agroupofnovel,carbazole-baseddendrimerscomprisedoftheelectron-acceptingdibenzothiophenecoreandtheelectron-donatingoligo-carbazoledendrons,namelyG1SFandG2SF,aresynthesizedutilizingtheUllmannC–Ncouplingreaction.Thedendrimersaredesignedinsuchawaytoshowgoodsolubilityincommonorganicsolvents,excellentthermochemicalstabilitywithdecompositiontemperatures(Td)upto4308C,andhighHOMOlevelsinarangefromÀ5.45eVtoÀ5.37eV.Resultsofdensityfunctionaltheorycalculations(DFT)indicateG2SFhasanalmostcompleteseparationofHOMOandLUMOlevelsatthehole-andelectron-transportingmoieties;whileG1SFexhibitsonlypartialseparationoftheHOMOandLUMOlevelspossiblyduetointramolecularchargetransfer.GreenphosphorescentOLEDswerefabricatedbythespincoatingmethodwiththedendrimersashostsandtraditionalgreeniridiumphosphorasdopedemitter.Underambientconditions,amaximumluminanceefficiency(hL)of19.83cdAÀ1andamaximumexternalquantumefficiencyof5.85%areachievedforG1SF,and15.50cdAÀ1and4.57%forG2SF.ß2016ChineseChemicalSocietyandInstituteofMateriaMedica,ChineseAcademyofMedicalSciences.PublishedbyElsevierB.V.Allrightsreserved.
*Correspondingauthor.E-mailaddress:tingzhang84@163.com(T.
Zhang).ContentslistsavailableatScienceDirect
ChineseChemicalLetters
journalhomepage:www.elsevier.com/locate/cclet
http://dx.doi.org/10.1016/j.cclet.2015.12.0281001-8417/ß2016ChineseChemicalSocietyandInstituteofMateriaMedica,ChineseAcademyofMedicalSciences.PublishedbyElsevierB.V.Allrightsreserved.carbazole,variousmoietiescapableofacceptingelectronswere
incorporatedtogivenovelbipolarhosts[22–24].Forexample,
Yangetal.reportedabipolardendrimerwithcarbazoleunitsas
hole-transportingunitsandoxadiazoleunitsaselectron-trans-
portingunitswithmaximumefficienciesof16.8cdAÀ1and5.7%