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%