TR201712311T1 - Organik Temelli Işık Yayan Diyotlar İçin Tiyenotiyofen Bor (Elektron Verici-Alıcı) Temelli Malzemeler - Google Patents

Organik Temelli Işık Yayan Diyotlar İçin Tiyenotiyofen Bor (Elektron Verici-Alıcı) Temelli Malzemeler Download PDF

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TR201712311T1
TR201712311T1 TR2017/12311T TR201712311T TR201712311T1 TR 201712311 T1 TR201712311 T1 TR 201712311T1 TR 2017/12311 T TR2017/12311 T TR 2017/12311T TR 201712311 T TR201712311 T TR 201712311T TR 201712311 T1 TR201712311 T1 TR 201712311T1
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organic
emitting diodes
boron
light emitting
thienothiophene
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Teki̇n Emi̇ne
Emi̇n Çinar Mehmet
Türkoğlu Gülşen
Ceyhan Gören Ahmet
Öztürk Turan
Buyruk Ali̇
Pi̇ravadi̇li̇ Mucur Seli̇n
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Tuerkiye Bilimsel Ve Teknolojik Arastirma Kurumu Tuebitak
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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Abstract

Mevcut buluş tiyenotiyofen (TT) ve bor türevlerinin bir serisinin belirtilen yapılara sahip yeni moleküllerini ve organik temelli ışık yayan diyotlara uygulanması beklenen ışık yayan cihazlarını açıklar.

Description

TARIFNAME ORGANIK TEMELLI ISIK YAYAN DIYOTLAR IÇIN TIYENOTIYOFEN BOR (ELEKTRON VERICI-ALICI) TEMELLI MALZEMELER BULUS ALANI: Mevcut çalisma tiyenotiyofen ve bor türevlerinin belirlenmis yapilariyla ilgilidir. Organik temelli isik yayan diyotlarda (OLED) uygulama potansiyeline sahiptirler. BULUSUN GEÇMISI Elli yildan fazladir, organik elektronik ve optoelektronik malzemeler artan sayida, özellikle, fizik ve kimya arastirmacilarinin ilgisi çekmektedir, bunun ana sebebi organik bilesiklerin kimyasal yapilarinin modifiye edilebilmelerinin yüksek olasiligidir. Nitekim, malzemelerin özellikleri direkt olarak degistirilebilir. l980°lerin ortasina kadar, organik malzemelerden yapilan aygitlarin kararlilik ve performanslari, silikon ya da galyum arseiiit gibi malzeme temelli aygitlardan geride kaldi. Düsük voltajli ve verimli ince filmli isik yayan diyotlarin çikmasiyla bu durum degisti. Bu,-yeni nesil elektronik ve optoelektronik aygitlar için organik ince filmlerin kullanim iinkanini sagladi. Organik ince filmlerin çesitli uygulamalarda kullanisli olmasi günümüzde kanitlanmaktadir; en basarili olani günümüzde renkli ekranlarda kullanilan organik temelli isik yayan diyotlardir (OLED). Genel olarak, iki grup organik malzeme; küçük moleküller ve polimerler, elektronik ve optoelektronik aygitlarda kullanilir, her ikisi de çözeltilerinden üretilebilir ve-düsük maliyetli aygit üretimine inikan saglar. Omegin, küçük molekül ve polimer elektro-luminesans cihazlar, C. W. Tang, tanimlanmistir. Yüksek performansli optik ve elektronik organik aygitlarin dizayni, elektronik yapilarinin anlasilmasini gerektirir ve hatta organik malzemenin içeriginde ve yapisindaki ufak bazi degisiklikler bile orijinal özelliklerini büyük oranda degistirebilir. Organik konjuge malzemelerin optoelektroiiik özelliklerini ayarlamak için yapilarinda gerçeklestirilen degisimler çaba isteyen bir konudur. Uygun moleküler düzenleme ile fonksiyonel özellikleri degisebilen tiyofen temelli organik malzemeler, en çok umut veren malzemeler arasindadir. Ornegin, oligotiyofenlerin ilgili oligotiyofen-S,S-dioksitlerine dönüstürülmesinin, hem ince film fotolüminesans verimliligini hem de moleküler enerji seviyelerini arttirdigi gösterilmistir: Son zamanlarda, organik elektronik ve optoelektronik malzemelerin özelliklerini degistirmek için bor atomu uygulanmistir ve bu ilgi çekici sonuçlar vermistir. Bor atomunun bos pZ orbitalinin varligi, üçlü bag yaptiginda güçlü elektron çekici olarak davranmasi, özelliklerin degisniesinin ana sebebidir. "Tr" sistemlere bagli oldugunda, elektronlari güçlü sekilde delokalize eder ve konjuge organoboranlar; elektronikler, optoelektronikler ve sensörlerde genis uygulamalar bulmasiyla, yeni bir sinif organik malzeme sayilirlar. Tiyofen, tiyofen türevleri ve bor gibi farkli fonksiyonel yapi bloklarinin kombinasyonlarina sahip olan malzemeler, tek aktif moleküler materyalden, beyaz isik yayma egilimindedir (M. Mazzeo, Adv. Mater. 2005, 17, 34). Topaklanmaya bagli emisyon (AIE: Aggregation-Induced Emission) dogasina ve desik iletici yetenegine sahip malzeme, tetrafeniletilen ve trifenilaniinden olusan, basit yapili ve düsük maliyetli fakat iyi performans gösteren organik temelli isik yayan diyotlarin üretimine imkan sagladi (Tang Z. B. Adv. Mater. 2010, 22, 19). Dogasi geregi elektronca fakir grup, dimestilboril, ile birlestirilen topaklanmaya bagli emisyon-aktif malzemeler, bu materyallerin organik isik yayan diyotlarda, ayni anda iki foksiyonlu isik yayan tabaka ve elektron Bundan dolayi, organik isik yayan diyotlarda çesitli emisyonlari elde etmek için tiyofen, tiyofen türevleri ve bora sahip olan malzemelerin gelistirilmesi arzu edilir. BULUSUN AÇIKLANMASI Bulus, organik temelli isik yayan malzemeler olarak (yani, organik temelli isik yayan diyotlar (OLED) kullanildiginda faydali olan bilesikleri açiklar. Organik alan etkili transistörler (OFET), organik fotovoltaik diyotlar ve benzeri elektronik cihazlarda yük transfer malzemeleri olarak kullanilma potansiyeline sahiptirler. Bulus (l) formüllerine sahip olan bilesikleri açiklar. Buradaki R1, R2 ve R3 1 atomdan 100 atoma kadar bagimsiz ya da ayni zincir(1er)/grup(lar)"dir. Bunlar ayni ya da bagimsiz olacak sekilde, dallanmis veya dallanmamis olarak alkil, aril, alkenil, alkinil, ainin, ester, karbonat esteri, karbonil, sulfit, organosilan ve tiyolattan olusan bir veya birden fazla gruba sahip olabilirler. Tiyenotiyofenler I (TT) literatür prosedürü takip edilerek sentezlendi (T. Ozturk, et al. 46, 9202 ). TT"ler I, TT II"lerin n-BuLi ile lityumlanmasi ve takiben arildimetoksibor eklenmesiyle elde edildi. difenilanilin (l) Sentezi Için Prosedür. 4-(3-(4-Metoksifenil)tiyeno[3,2-b]tiyofen-2-il)-N,N- umol) azot atmosferi altinda -78 0C"de damla damla eklendi. Reaksiyon karisimi bir saat ayni sicaklikta karistirildi. Sonrasinda, -78 0C"de MesB(OMe)2 ( eklendi ve çözelti yavasça oda sicakligina isitildi ve sonrasinda bir 12 saat daha karistirildi. Urün diklorametan (3 X20 mL) ile ekstrakte edildi. Çözelti tuzlu su ve su ile yikandi ve sonrasinda NaZSO4 üzerinde kurutuldu. Atmosfer basinci altinda solvent uçurulduktan sonra, ham ürün silika jel üzerinde eluent olarak n-hegzan/diklorametan (6:1) karisimi kullanilarak kolon kromatografisi ile saflastirildi. Urün yesil renkli bir kati madde olarak %45 verimle elde edildi; Rf:, 7.38 (d, Cihaz Uretim Ornegi: Organik temelli isik yayan diyotlar küçük moleküllerin iletken yüzey üzerine çözeltilerinden kaplanmasi ile üretildi. Molekül (1) toluene/diklorametan (8 mg/ml) karisiminda çözüldü. Indiyum kalay oksit (ITO), cam yüzey üzerine (15 ohms/sq.) kaplanan, anot elektrot olarak kullanildi. PEDOTzPSS, desik enjeksiyon tabakasi olarak, indiyum kalay oksit üzerine döndürmeli olarak kaplandi ve 110 °C"de 10 dakika kurutuldu. Ardindan, molekül filmi, aktif tabaka olarak, dönerek kaplama ile kaplandi. Son olarak, LiF (l nm) ve alüminyum (A1, 100 nm) vakum altinda (~1076 mbar) termal buharlastirma teknigi ile katot elektrodu elde etmek için biriktirildi. Çizimlerin Açiklanmasi Sekil 1. Molekül (l)°in oda sicakliginda tetrahidrofurandaki (THF) UV-Vis spektrumu. Sekil 2. Molekül (I)"in oda sicakliginda tetrahidrofuraiidaki (THF) ve kati haldeki (ITO kaplanmis cam) floresans spektrumlari. Sekil 3. a) Molekül (I)"in üretilen cihazinin elektrolüminesans spektrumu (cihaz tasarimi: PEDOT/Molekül(l*)/LiF/Al); b) Molekül (l)"in üretilen cihazinin farkli voltajlardaki CIE koordinatlari. Elektrolüminesans spektrumu yaklasik 400 nm°den 650 nm"ye kadarki bölgeyi kapsamaktadir, CIE 1931 Renk Diagramina göre renk koordinatlari mavi-yesil bölgesindedir. Sekil 4. OLED cihaz karakteristikleri: a) voltaj-akim b) luminans-voltaj c) parlaklik verimi- akim yogunlugu d) dis kuantum verimliligi-akim yogunlugu. Normalize Absorbans [a.u.] 350 I 400 Dalga Boyu [nm] Normalize Floresans [a.u.] + THF'de Floresans -i- lTO'da Floresans Dalga Boyu [nm] Normalize EL Yogunlugu [a.u.] Renk Koordinatlari x,y Dalga Boyu [nm] 0.40 - 0.35 - o . 7,. 77 i 0.30 - 0.20 - i 0.15 I I I I ' I I I Voltage [V] 58035_ :m:_::mo EE< Akim Yogunlugu [mA/cm2] Voltaj [V] 2 o 8 6 4 2 Voltaj [V] Voltaj [V] TR TR TR TR TR TR TR TR TR TR TR
TR2017/12311T 2015-02-20 2015-02-20 Organik Temelli Işık Yayan Diyotlar İçin Tiyenotiyofen Bor (Elektron Verici-Alıcı) Temelli Malzemeler TR201712311T1 (tr)

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US10000513B2 (en) 2018-06-19
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WO2016132180A1 (en) 2016-08-25

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