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 PDFInfo
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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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- 239000000463 material Substances 0.000 title claims description 16
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 title abstract description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title description 5
- 229910052796 boron Inorganic materials 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- -1 carbonate ester Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000001282 organosilanes Chemical class 0.000 claims description 2
- 238000005424 photoluminescence Methods 0.000 claims description 2
- 150000007944 thiolates Chemical class 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000004020 conductor Substances 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 claims 1
- 150000001638 boron Chemical class 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 230000005693 optoelectronics Effects 0.000 description 6
- 239000011368 organic material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- VYMUGTALCSPLDM-UHFFFAOYSA-L carbasalate calcium Chemical compound [Ca+2].NC(N)=O.CC(=O)OC1=CC=CC=C1C([O-])=O.CC(=O)OC1=CC=CC=C1C([O-])=O VYMUGTALCSPLDM-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 239000002120 nanofilm Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- 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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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]
Claims (3)
1- (I) formüllü bilesik. Buradaki R1, R2 ve R3 1 atoindan 100 atoma kadar bagimsiz ya da ayni zincir(ler)/grup(lar)”dir, bunlar ayni ya da bagimsiz olacak sekilde, dallanmis veya dallanmamis alkil, aril, alkenil, alkinil, amin, ester, karbonat esteri, karbonil, sulfit, organosilan ve tiyolattan olusan bir veya birden
2-Istem 1'de verilen bilesiklerden olusan formülasyon
3-Istem lsde verilen bilesigi içeren formülasyonun, elektronik, optik, elektrooptik, elektrolüminesans ya da fotol'i'iminesans bilesenleri ya da cihazlarinda yük transferi, elektrik iletkeni, yariiletken, fotoiletken ya da isik yayan inalzeme olarak kullanilmasi.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IB2015/051306 WO2016132180A1 (en) | 2015-02-20 | 2015-02-20 | Thienothiophene and dithienothiophene - boron (donor-acceptor) based materials for organic light emitting diodes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TR201712311T1 true TR201712311T1 (tr) | 2018-03-21 |
Family
ID=52785142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TR2017/12311T TR201712311T1 (tr) | 2015-02-20 | 2015-02-20 | Organik Temelli Işık Yayan Diyotlar İçin Tiyenotiyofen Bor (Elektron Verici-Alıcı) Temelli Malzemeler |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10000513B2 (tr) |
| EP (1) | EP3259275B1 (tr) |
| JP (1) | JP6621850B2 (tr) |
| KR (1) | KR102349846B1 (tr) |
| CA (1) | CA2977171C (tr) |
| TR (1) | TR201712311T1 (tr) |
| WO (1) | WO2016132180A1 (tr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102349852B1 (ko) * | 2015-02-20 | 2022-01-10 | 티유비아이티에이케이 | 유기발광 다이오드용 티에노티오펜/다이티에노티오펜 - 트라이페닐아민/테트라페닐에틸렌 유도체 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356429A (en) | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
| GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| US6727008B1 (en) | 1997-04-30 | 2004-04-27 | Agilent Technologies, Inc. | Oxadiazole blue-emitting organic LED's |
| DE60236912D1 (de) | 2001-09-29 | 2010-08-19 | Merck Patent Gmbh | Mono-, Oligo- und Polymere aus Benzo(b)thiophen und 2,2'-bisbenzothiophen und ihre Verwendung als Ladungstransportmaterial |
| DE60116330T2 (de) | 2001-11-09 | 2006-12-14 | Simonazzi S.P.A. | Abfüllventil für Abfüllmaschine |
| US7133032B2 (en) | 2003-04-24 | 2006-11-07 | Eastman Kodak Company | OLED display and touch screen |
| WO2007134280A1 (en) | 2006-05-12 | 2007-11-22 | University Of Utah | π-CONJUGATED HEAVY-METAL POLYMERS FOR ORGANIC WHITE-LIGHT-EMITTING DIODES |
| JP2010513611A (ja) | 2006-12-22 | 2010-04-30 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 縮合したセレノフェンを含むポリマー |
| KR101324785B1 (ko) * | 2011-02-22 | 2013-10-31 | (주)씨에스엘쏠라 | 유기발광화합물 및 이를 이용한 유기 광소자 |
| KR101324150B1 (ko) * | 2011-05-17 | 2013-11-01 | (주)위델소재 | 유기전계 발광 재료용 아릴아민유도체와 이를 제조하는 방법 및 유기전계 발광 재료용 아릴아민유도체를 포함하는 유기전계 발광 재료 |
| EP2850668B1 (en) * | 2012-05-15 | 2019-11-20 | Nissan Chemical Corporation | Hole transport materials including oled applications |
| US9831441B2 (en) | 2012-10-31 | 2017-11-28 | Merck Patent Gmbh | Electronic device |
| CN103896973B (zh) * | 2014-04-11 | 2018-01-30 | 中国科学院理化技术研究所 | 二（三甲苯基）硼衍生物及其在白光有机电致发光二极管中的应用 |
| KR102349852B1 (ko) * | 2015-02-20 | 2022-01-10 | 티유비아이티에이케이 | 유기발광 다이오드용 티에노티오펜/다이티에노티오펜 - 트라이페닐아민/테트라페닐에틸렌 유도체 |
-
2015
- 2015-02-20 JP JP2017562142A patent/JP6621850B2/ja active Active
- 2015-02-20 EP EP15712419.9A patent/EP3259275B1/en active Active
- 2015-02-20 US US15/552,492 patent/US10000513B2/en active Active
- 2015-02-20 WO PCT/IB2015/051306 patent/WO2016132180A1/en active Application Filing
- 2015-02-20 TR TR2017/12311T patent/TR201712311T1/tr unknown
- 2015-02-20 CA CA2977171A patent/CA2977171C/en active Active
- 2015-02-20 KR KR1020177025191A patent/KR102349846B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| KR20170137053A (ko) | 2017-12-12 |
| JP2018508576A (ja) | 2018-03-29 |
| JP6621850B2 (ja) | 2019-12-18 |
| WO2016132180A1 (en) | 2016-08-25 |
| CA2977171C (en) | 2022-07-12 |
| EP3259275B1 (en) | 2020-06-10 |
| EP3259275A1 (en) | 2017-12-27 |
| US20180030069A1 (en) | 2018-02-01 |
| US10000513B2 (en) | 2018-06-19 |
| CA2977171A1 (en) | 2016-08-25 |
| KR102349846B1 (ko) | 2022-01-10 |
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