TW202016079A - 苯基聯苯嘧啶類化合物及其有機電激發光元件 - Google Patents
苯基聯苯嘧啶類化合物及其有機電激發光元件 Download PDFInfo
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- TW202016079A TW202016079A TW107137368A TW107137368A TW202016079A TW 202016079 A TW202016079 A TW 202016079A TW 107137368 A TW107137368 A TW 107137368A TW 107137368 A TW107137368 A TW 107137368A TW 202016079 A TW202016079 A TW 202016079A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 14
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
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- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 6
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
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- PNEPKYMMFZQVKA-UHFFFAOYSA-N 1,1'-biphenyl;pyrimidine Chemical class C1=CN=CN=C1.C1=CC=CC=C1C1=CC=CC=C1 PNEPKYMMFZQVKA-UHFFFAOYSA-N 0.000 claims 1
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- 125000001424 substituent group Chemical group 0.000 description 4
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- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 2
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- XMQNXCFNVDKLNB-UHFFFAOYSA-N [N-]=[N+]=[N-].[N-]=[N+]=[N-].[Li+] Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].[Li+] XMQNXCFNVDKLNB-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001964 alkaline earth metal nitrate Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical class Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- VNSVQJIXVXZDJF-UHFFFAOYSA-L dilithium;phthalate Chemical compound [Li+].[Li+].[O-]C(=O)C1=CC=CC=C1C([O-])=O VNSVQJIXVXZDJF-UHFFFAOYSA-L 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000001912 gas jet deposition Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 description 1
- 229960000761 pemoline Drugs 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- UCBCBMOOIZMOTR-UHFFFAOYSA-N pyrazine;pyridine Chemical compound C1=CC=NC=C1.C1=CN=CC=N1 UCBCBMOOIZMOTR-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- OWECKHSCCDVJCN-UHFFFAOYSA-N quinazoline;quinoxaline Chemical compound N1=CN=CC2=CC=CC=C21.N1=CC=NC2=CC=CC=C21 OWECKHSCCDVJCN-UHFFFAOYSA-N 0.000 description 1
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical group [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
- 229910000026 rubidium carbonate Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
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Abstract
一種具式(I)結構之苯基聯苯嘧啶類化合物及使用該化合物之有機電激發光元件,其中,X1、A1及n係如同說明書中之定義。
Description
本發明係關於一種用於有機電激發光元件之材料及使用該材料之有機電激發光元件。
近來,有機電激發光元件(OLED)在高發光率的高密度畫素顯示器上因具備長壽命、高效率、低驅動電壓、色域廣及成本低等優勢,而具有商業性吸引力,為滿足該有機電激發光元件之應用,特別著重其新穎的有機材料之開發。
典型的OLED至少一夾置於陽極與陰極間之有機發射層(organic emissive)層。當施加電流時,陽極注入電洞且陰極注入電子至該一層或多層有機發射層,被注入的電洞及電子各自遷移至相反的帶電荷電極。當電子及電洞侷限在相同的分子上時,形成”激子(exciton)”,該激子係具有受激發能態的侷限化電子一電洞對,通過發光機制該激子鬆弛而發射光。為求提升此等元件的電荷傳輸能力及發光效率,於發光層旁結合一層或多層之額外層體,例如電子
傳輸層及/或電洞傳輸層,或電子阻擋層及/或電洞阻擋層。文獻中,已充分證明在主體材料摻混另一客體材料,以提升裝置性能及調整色度。全文併入本文參考的第4769292、5844363、5707745、6596415及6465115號美國專利中敘述了幾種OLED材料和裝置組構。昱鐳光電科技已經在2016年申請並於2017年獲證中華民國專利號I582081,此專利所介紹的電子傳輸材料已經具有一定的新穎性與效果,而本新申請專利的效果更勝於此前案。
製造具多層薄膜結構OLED之原因包含使該等電極及有機層之間之界面安定及有機材料的搭配。在有機材料中,其電子及電洞之遷移率(mobility)明顯不同,若使用相稱之電洞傳輸及電子傳輸層,電洞及電子可有效地傳輸至該發射層,使該發射層中該電子及電洞之密度平衡,增加發光效率。適當之結合該上述有機層可增進該元件效率及壽命。然而,仍難以找到滿足所有實際顯示器應用之需求的有機材料,尤係用於車用顯示器或是照明光源之有機材料,需具備耐高溫與長壽命的性質,常見的有機材料大多僅耐溫至100℃。
因此,亟需一種有機材料可顯著改善有機電激發光元件的壽命並提高載子遷移率,以符合多樣化應用的需求。
本發明之目的在於提供種具有較長壽命、高載子遷移率及耐熱性佳之用於有機電激發光元件之材料。
其中,X1及A1為相同或相異且各獨立表示經取代或未經取代之C6-30芳基或經取代或未經取代之含有選自由N、O、及S所組成群組中之至少一雜原子之C5-30雜芳基;以及n表示1或2之整數,當n表示1且A1為未經取代之苯基時,該A1係鍵結於相對嘧啶部分之對位位置;當n表示2時,A1各自為相同或相異。
於本發明具式(I)結構之苯基聯苯嘧啶類化合物之一具體實施態樣中,X1係選自由未經取代之吡啶基、經鹵素取代之苯基及經C1-4烷基取代之苯基所組成群組中之一者。例如,具式(I)結構之苯基聯苯嘧啶類化合物,係選自由下列所組成群組中之一者:
於本發明具式(I)結構之苯基聯苯嘧啶類化合物之一具體實施態樣中,A1為經取代或未經取代之C9-30稠合多環芳香烴基(fused polycyclic aromatic)、具有螺狀結構之經取代或未經取代之C9-30芳香烴基或經取代或未經取代之含有選自由N、O、及S所組成群組中之至少一雜原子之C5-30稠合多環芳香烴基。
更具體而言,A1係選自下列所組成群組中之一者:
其中,Ar1表示未經取代之C6-18伸芳基或連接於式(I)化合物之單鍵;Ar2表示氫或未經取代之C6-18芳基;L表示N、N-R1、O或S,且R1為未經取代之C6-18
芳基;以及L1表示N或N-R2,且R2為連接於式(I)化合物之未經取代之C6-18伸芳基。
其中,該A1各自為相同或相異。
本發明復提供一種有機電激發光元件,包含:陰極;陽極;以及有機層,係介於該陰極與陽極之間,且該有機層係包含本發明之具式(I)結構之苯基聯苯嘧啶類化合物。
於本發明有機電激發光元件之一具體實施態樣中,該有機層係電子傳輸層,且其厚度係20奈米至30奈米。此外,該電子傳輸層可復包含N型電性傳導摻質,且該N型電性傳導摻質的含量為大於0重量%至50重量%。例如,該N型電性傳導摻質為喹啉鋰。
於本發明有機電激發光元件之一具體實施態樣中,該有機層復包括電洞阻擋層,且其厚度係大於0奈米至5奈米。
根據本發明,藉由本發明提供之具式(I)結構之苯基聯苯嘧啶類化合物,其聯苯基與嘧啶部分之鍵結位置相較其
他鍵結位置更可有效改善所製之有機電激發光元件的壽命、提高載子遷移率,並提供良好耐熱性之好處。
100、200、300‧‧‧有機電激發光元件
110、210、310‧‧‧基板
120、220、320‧‧‧陽極
130、230、330‧‧‧電洞注入層
140、240、340‧‧‧電洞傳輸層
150、250、350‧‧‧發光層
160、260、360‧‧‧電子傳輸層
170、270、370‧‧‧電子注入層
180、280、380‧‧‧陰極
245、345‧‧‧電子阻擋層
355‧‧‧電洞阻擋層
透過例示性之參考附圖說明本發明的實施方式:第1圖係本發明之有機電激發光元件之一實施例之剖面示意圖;第2圖係本發明之有機電激發光元件之另一實施例之剖面示意圖;以及第3圖係本發明之有機電激發光元件之又一實施例之剖面示意圖。
以下係藉由特定的具體實施例說明本發明之實施方式,熟習此技藝之人士可由本說明書所揭示之內容輕易地瞭解本發明之優點及功效。本發明亦可藉由其它不同之實施方式加以施行或應用,本說明書中的各項細節亦可基於不同觀點與應用,在不悖離本發明所揭示之精神下賦予不同之修飾與變更。此外,本文所有範圍和值都係包含及可合併的。落在本文中所述的範圍內之任何數值或點,例如任何整數都可以作為最小值或最大值以導出下位範圍等。
文中,表達成「經取代或未經取代之」中的「經取代之」表示在某個官能基中之氫原子係經另一個原子或基團(即取代基)置換。該等取代基各自獨立地選自由下列所組成之群組中之至少一者:氘、鹵素、C1-30烷基、C1-30烷氧基、C6-30芳基、C5-30雜芳基、經C6-30芳基取代之C5-30雜芳
基、苯並咪唑基、C3-30環烷基、C5-7雜環烷基、三C1-30烷基矽烷基、三C1-30芳基矽烷基、二C1-30烷基C6-30芳基矽烷基、C1-30烷基二C6-30芳基矽烷基、C2-30烯基、C2-30炔基、氰基、二C1-30烷基胺基、二C6-30芳基硼基、二C1-30烷基硼基、C1-30烷基、C6-30芳基C1-30烷基、C1-30烷基C6-30芳基、羧基、硝基及羥基。
於一具體實施態樣中,該C6-30芳基係經選自由鹵素、C1-5烷基、C6-30芳基及C5-30雜芳基所組成群組中之至少一者的取代基取代。
於另一具體實施態樣中,該C6-30芳基係經選自由鹵素、甲基、苯基、苯并咪唑基及咔唑基所組成群組中之至少一者的取代基取代。
於一具體實施態樣中,該含有選自由N、O、及S所組成群組中之至少一雜原子之C5-30雜芳基係由C6-30芳基取代基取代。
於另一具體實施態樣中,該C6-30芳基係經苯基取代基取代。
文中,「芳基」表示芳基或(伸)芳基,該芳基係指衍生自芳香烴的單環系環或稠合環,及包括苯基、聯苯基、聯三苯基(terphenyl)、萘基、聯萘基、苯基萘基、萘基苯基、茀基(fluorenyl)、苯基茀基、苯并茀基、二苯并茀基、菲基、苯基菲基、蒽基、茚基、聯伸三苯基(triphenylenyl)、芘基、稠四苯基、苝基、蒯基(chrysenyl)、萘并萘基、丙二烯合茀基(fluoranthenyl)等。
文中,「雜芳基」表示雜芳基或(伸)雜芳基,該雜芳基係指含有選自由N、O、及S所組成群組中之至少一個雜原子的環主鏈原子的芳基,可為單環系環,如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異唑基(Isoxazole)、唑基(oxazole)、二唑基(oxadiazole)、三基(triazine)、四基(tetrazine)、三唑基(triazole)、四唑基(tetrazole)、呋呫基(furazanyl)、吡啶基、吡基(pyrazine)、嘧啶基、嗒基(pyridazine)等,或為與至少一個苯環縮合的稠合環,如苯并呋喃基、苯并噻吩基、異苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異唑基、喹啉基、異喹啉基、啉基(cinnoline)、喹唑啉基(quinazoline)、喹啉基(quinoxaline)、咔唑基(carbazole)、啡唑基(phenoxazole)、啡啶基(phenanthridine)、苯并二呃基(benzodioxolyl)、二氫吖啶基(dihydroacridine)等。
於一具體實施態樣中,前述具式(I)結構之苯基聯苯嘧啶類化合物之較佳實施例係選自於表1,但不限於此。
以下說明式(I)之苯基聯苯嘧啶類化合物之一實施例的典型合成途徑,但合成所述式(I)之苯基聯苯嘧啶類化合物之反應不限於此。
分別加入4-溴苯甲醛、3-聯苯乙酮與乙醇入反應瓶中攪拌,再加叔丁醇鈉(Sodium tert-Butoxide,NaOtBu)或氫氧化鈉至反應瓶中一起攪拌後,於室溫下反應隔夜。待反應完全後,加入去離子水經攪拌後過濾,使濾得的固體先以去離子水及甲醇進行清洗,再以去離子水及甲醇經攪拌後過濾,並使上述清洗過濾步驟重複2次後,乾燥即得白色中間體A。
中間體A與不同的甲脒鹽酸鹽衍生物及乙醇加入反應瓶中攪拌,再加入叔丁醇鈉或氫氧化鈉至反應瓶中一起攪拌後,,開啟加熱攪拌並維持80℃進行回流。待反應完成後,使反應降溫至60℃,加入去離子水並攪拌後,移除水層,將有機層濃縮直至固體析出,再經乙酸乙酯沖洗、過濾及乾燥後,獲得白色中間體B。
將中間體B與不同的硼酸衍生物及碳酸鉀置於反應瓶,再加入四氫呋喃及去離子水,使反應瓶置於油浴中,並連接氮氣及冷凝管後,開啟加熱攪拌80℃,同時,加入四(三苯基膦)鈀(Pd(PPh3)4)於反應瓶中,進行回流。待反應完全且有固體析出時,移除油浴,使其降溫後進行過濾,使濾得的濾餅再加入去離子水,經攪拌後進行再過濾,並再將濾得的濾餅加入四氫呋喃,經加熱攪拌直至全溶後,加入一含有氧化矽之管柱進行層析純化,並濃縮至白色固體析出,再經乙酸乙酯沖洗、過濾及乾燥後,獲得白色固體,即為產物。
本發明復提供一種有機電激發光元件,包含:陰極;
陽極;以及有機層,係介於該陰極與陽極之間,且該有機層包含本發明之具式(I)結構之苯基聯苯嘧啶類化合物。
本發明之有機電激發光元件之該有機層係可為電子傳輸層、電子注入層、發光層、電洞阻擋層或電子阻擋層,且除了該有機層外,該有機電激發光元件復可包括不同於該有機層的選自由電子傳輸層、電子注入層、發光層、電洞阻擋層及電子阻擋層所組成群組的至少一層,其中,該發光層復包含螢光或磷光摻質,以及分別對應螢光或磷光摻質之主體材料。
於一具體實施態樣中,包含上述之具式(I)結構之苯基聯苯嘧啶類化合物之有機層較佳為電子傳輸層,且其厚度係20奈米至30奈米;其中,該電子傳輸層可將具式(I)結構之苯基聯苯嘧啶類化合物做為單一材料,或將具式(I)結構之苯基聯苯嘧啶類化合物與電性傳導摻質結合使用。
於另一具體實施態樣中,該電子傳輸層復包含N型電性傳導摻質,其中,該N型電性傳導摻質與本發明之具式(I)結構之苯基聯苯嘧啶類化合物產生螯合作用(chelation),可使電子更容易地從陰極注入到電子傳輸層中,解決了現有技術中因金屬與電子傳輸主體材料的相容性較差而導致的相分離以及形成淬熄中心的問題,有效提高了電子傳輸層的電子傳輸效率。
應用於電子傳輸層之N型電性傳導摻質係可為有機鹼金屬/鹼土金屬之硝酸鹽、碳酸鹽、磷酸鹽或喹啉酸鹽。具體而言,如碳酸鋰、喹啉鋰(lithium quinolate,Liq)、疊氮
化鋰(lithium azide)、碳酸銣、硝酸銀、硝酸鋇、硝酸鎂、硝酸鋅、硝酸銫、碳酸銫、氟化銫、疊氮化銫等,其中,該N型電性傳導摻質尤以喹啉鋰為佳。
於一具體實施態樣中,以該電子傳輸層之重量計算,該N型電性傳導摻質的含量為大於0重量%至50重量%。
於一具體實施態樣中,包含上述之具式(I)結構之苯基聯苯嘧啶類化合物之有機層係為電子傳輸層及電洞阻擋層之疊合,其中,該電洞阻擋層厚度係大於0奈米至5奈米。
於另一具體實施態樣中,該疊合有機層之電洞傳輸層係以具式(I)結構之苯基聯苯嘧啶類化合物做為單一材料,而該疊合有機層之電子傳輸層係使用具式(I)結構之苯基聯苯嘧啶類化合物結合N型電性傳導摻質。
本發明之有機電激發光元件之結構將配合圖式加以說明。
第1圖係本發明之有機電激發光元件之一具體實施例之剖面示意圖。有機電激發光元件100包含基底110、陽極120、電洞注入層130、電洞傳輸層140、發光層150、電子傳輸層160、電子注入層170及陰極180。有機電激發光元件100可經由依序沉積上述各層來製作。
第2圖係本發明之有機電激發光元件之另一具體實施例之剖面示意圖。有機電激發光裝置200包含基板210、陽極220、電洞注入層230、電洞傳輸層240、電子阻擋層245、發光層250、電子傳輸層260、電子注入層270及陰極280,與第1圖之差異在於該電子阻擋層245係設於電
洞傳輸層240與發光層250之間。
第3圖係本發明之有機電激發光元件之又一具體實施例之剖面示意圖。有機電激發光裝置300包含基板310、陽極320、電洞注入層330、電洞傳輸層340、電子阻擋層345、發光層350、電洞阻擋層355、電子傳輸層360、電子注入層370及陰極380,與第2圖之差異在於該電洞阻擋層355係設於發光層與電子傳輸層360之間。
可依第1圖至第3圖所示元件之反置式結構(reverse structure)製造有機電激發光元件。於該等反置式結構可視需求增減一層或數層。
所述之電洞注入層、電洞傳輸層、電子阻擋層、電洞阻擋層、電子阻擋層、電子注入層之材料可選擇習用材料,舉例來說,形成電子傳輸層之電子傳輸材料不同於發光層之材料,且其具有電洞傳輸性,從而促成電洞於電子傳輸層中遷移,且防止因發光層與電子傳輸層之解離能差所導致的載子累積。
本發明之具式(I)結構之苯基聯苯嘧啶類化合物用於電子傳輸層或電洞阻擋層,因具有高於2.4eV之三重態能量(ET)、極低最高佔據分子軌道(HOMO)之能階及良好的載子遷移率,使發光層內電洞不易流失,並同時使電子有效地傳輸至該發光層,有助於發光層中該電子及電洞之密度平衡,增加發光效率及驅動穩定性。
此外,第5844363號美國專利揭示一種結合陽極之可撓性透明基底,其全部內容為本發明所引用。如第
20030230980號美國專利所例示p型摻雜之電洞傳輸層係以莫耳比50:1於m-MTDATA摻雜F4-TCNQ,其全部內容為本發明所引用。如第20030230980號美國專利所例示n型摻雜之電子傳輸層係以莫耳比1:1於BPhen摻雜鋰,其全部內容為本發明所引用。如第5703436及5707745號美國專利所例示陰極之全部內容為本發明所引用,該陰極具有金屬薄層,如:鎂/銀(Mg:Ag),及以濺鍍沉積覆蓋金屬薄層之透明導電層(ITO Layer)。第6097147及20030230980號美國專利所揭示各阻擋層之應用及原理,其全部內容為本發明所引用。第20040174116號美國專利所例示之注入層及同案所說明之保護層,其全部內容為本發明所引用。
未特別說明之結構及材料亦可應用於本發明,如第5247190號美國專利所揭示包括聚合物材料(PLEDs)之有機電激發光元件,其全部內容為本發明所引用。再者,具有單一有機層之有機電激發光元件或如第5707745號美國專利所揭示堆疊形成之有機電激發光元件,其全部內容為本發明所引用。
除有特別限定,不同實施例中之任何層可使用任何適當方法來沉積形成。以有機層而言,較佳之方法包含如第6013982及6087196號美國專利所揭示之熱蒸鍍法及噴印法,其全部內容為本發明所引用;第6337102號美國專利所揭示有機氣相沉積法(organic vapor phase deposition,OVPD),其全部內容為本發明所引用;第10/233470號美國專利所揭示有機氣相噴印沉積法
(deposition by organic vapor jet printing,OVJP),其全部內容為本發明所引用。其他適當方法包含旋轉塗佈及以溶液為基礎之製程。以溶液為基礎之製程較佳是在氮氣或惰性氣體環境中進行。對於其他之層而言,較佳之方法包含熱蒸鍍法。較佳的圖案化方法包含如第6294398及6468819號美國專利所揭示通過遮罩沉積再冷焊之製程,及整合噴印或有機氣相噴印沉積與圖案化之製程,其全部內容為本發明所引用。當然亦可使用其他方法。用於沉積之材料可予調整以對應其所特用之沉積方法。
本發明具式(I)結構之苯基聯苯嘧啶類化合物係能以真空沉積或旋轉塗佈法製成應用於有機電激發光元件之非晶性薄膜。當該化合物使用於任一之上述有機層,其展現出較長使用壽命及良好的熱穩定性。
本發明之有機電激發光元件可應用於單一元件,其結構為陣列配置或陣列X-Y座標中設有陰陽兩極之元件。相較於習知元件,本發明能顯著提升有機電激發光元件之使用壽命。
以下藉由實施例詳細說明本發明之諸多性質及功效。該等詳述實施例僅用於說明本發明之性質,本發明部限於特定實施例所例示者。
合成例1:化合物2-1之合成
將3-聯苯乙酮(3-Acetylbiphenyl)(30g,164.6mmole)、3-溴苯甲醛(3-bromobenzaldehyde)(29.01g,156.79mmole)、600毫升的乙醇加入反應瓶內攪拌,再加入叔丁醇鈉(Sodium tert-butoxide)(22.58g,235.19mmole)於室溫下進行攪拌。待反應完全後,加入200毫升的去離子水經攪拌後過濾,使濾得的固體先以去離子水及甲醇進行清洗,再以100毫升的去離子水及200毫升的甲醇經攪拌30分鐘後過濾,並使上述清洗過濾步驟重複2次後,使固體乾燥後得白色固體(約52g),即為1-聯苯-3-基-3-(3-溴苯基)-丙烯酮(1-Biphenyl-3-yl-3-(3-bromo-phenyl)-propenone),產率92.3%。
將1-聯苯-3-基-3-(3-溴苯基)-丙烯酮(1-Biphenyl-3-yl-3-(3-bromo-phenyl)-propenone)(52g,143.15mmole)、4-甲基苯甲脒鹽酸鹽(4-methylbenzamidine hydrochloride)(26.87g,
157.47mmole)與氫氧化鈉(8.56g,214.73mmole)、78毫升的甲苯、260毫升的乙醇置於反應瓶內,開啟加熱攪拌並維持80℃進行回流。待反應完成後,使反應降溫至60℃,加入100毫升的去離子水並攪拌5分鐘後,移除水層,將有機層濃縮直至固體析出,再經乙酸乙酯沖洗、過濾及乾燥後,獲得白色固體(約27.7g),產率39.6%。
將4-聯苯-3-基-6-(3-溴苯基)-2-對甲苯基-嘧啶(4-Biphenyl-3-yl-6-(3-bromo-phenyl)-2-p-tolyl-pyrimidine)(4.32g,12mmole)與螺芴-2-硼酸(Spiro-9,9'-bifluorene-2-boronic acid)(4.78g,10mmole)及碳酸鉀(6.73g,35mmole)置於反應瓶,再加入34毫升的甲苯、10毫升的乙醇、14毫升的去離子水,使反應瓶置於油浴中,並連接氮氣及冷凝管後,開啟加熱攪拌80℃,同時,加入四(三苯基膦)鈀(Pd(PPh3)4)(0.58g,0.5mmole)於反應瓶中。待反應完全且有固體析出時,移除油浴,使其降溫後進行過濾,使濾得的濾餅再加入100毫升的去離子水,經攪拌10分鐘後進行再過濾,並再將濾得的濾餅加入250毫升的四氫呋喃,經加熱攪拌直至全溶後,加入一含有20克氧化矽之管柱進行
層析純化,並濃縮至白色固體析出,再經乙酸乙酯沖洗、過濾及乾燥後,獲得白色固體(約6.1g)即為產品,產率85.5%。
1H NMR(CDCl3,400MHz),δ8.56(d,2H),8.44(t,1H),8.36(t,1H),8.22(t,1H),8.14(t,1H),7.98(d,2H),7.90(d,1H),7.86(d,2H),7.73-7.77(m,2H),7.69-7.72(m,2H),7.63(t,1H),7.56(t,1H),7.47-7.53(m,3H),7.32-7.45(m,6H),7.11-7.15(m,3H),7.04(t,1H),6.81(d,2H),6.76(d,1H),2.47(s,3H).
合成例2:化合物2-2之合成
將3-聯苯乙酮(3-Acetylbiphenyl)(19.6g,100mmole)和4-溴苯甲醛(4-bromo-benzaldehyde)(18.5g,100mmole)放入500毫升的雙頸圓底反應瓶內,並分別加入200毫升的乙醇及氫氧化鉀(2.8g,50mmole)後,於室溫下進行攪拌。待反應完全後過濾固體,並以乙醇清洗並乾燥,獲得淡黃色固體(約31.3克),產率86%。
將1-聯苯-3-基-3-(4-溴苯基)-丙烯酮(1-Biphenyl-3-yl-3-(4-bromo-phenyl)-propenone)(51g,140.4mmole)、4-甲基苯甲脒鹽酸鹽(4-methylbenzamidine hydrochloride)(26.35g,154.44mmole)與氫氧化鈉(8.42g,210.6mmole)、77毫升的甲苯、255毫升的乙醇置於反應瓶內,開啟加熱攪拌並維持80℃進行回流。待反應完成後,使反應降溫至60℃,加入100毫升的去離子水並攪拌5分鐘後,移除水層,將有機層濃縮直至固體析出,再經乙酸乙酯沖洗、過濾及乾燥,獲得白色固體(約27g),產率40.28%。
將4-聯苯-3-基-6-(4-溴苯基)-2-對甲苯基-嘧啶(4-Biphenyl-3-yl-6-(4-bromo-phenyl)-2-p-tolyl-pyrimidine)(4.32g,12mmole)與9,9'-螺二芴-2-基硼酸(Spiro-9,9'-bifluorene-2-boronic acid)(4.78g,10mmole)及碳酸鉀(6.73
g,35mmole)置於反應瓶,再加入34毫升的甲苯、10毫升的乙醇,14毫升的去離子水,使反應瓶置於油浴中,並連接氮氣及冷凝管後,開啟加熱攪拌80℃,同時,加入四(三苯基膦)鈀(Pd(PPh3)4)(0.58g,0.5mmole)於反應瓶。待反應完全且有固體析出時,移除油浴,使其降溫後進行過濾,使濾得的濾餅再加入100毫升的去離子水,經攪拌10分鐘後進行再過濾,並再將濾得的濾餅加入250毫升的四氫呋喃,經加熱攪拌直至全溶後,加入一含有20克氧化矽之管柱進行層析純化,並濃縮至白色固體析出,再經乙酸乙酯沖洗、過濾及乾燥後,獲得白色固體(約6.3g),產率88.3%。
1H NMR(CDCl3,400MHz),δ8.60(d,2H),8.45(t,1H),8.25(d,2H),8.22(d,1H),7.98(s,1H),7.95(d,1H),7.88(t,3H),7.69-7.76(m,4H),7.60-7.64(m,3H),7.50(t,2H),7.38-7.43(m,4H),7.33(d,2H),7.13(t,3H),7.03(s,1H),6.81(d,2H),6.75(d,1H),2.45(s,3H).
合成例3:化合物2-4之合成
將4-聯苯-3-基-6-(4-溴苯基)-2-對甲苯基-嘧啶
(4-Biphenyl-3-yl-6-(4-bromo-phenyl)-2-p-tolyl-pyrimidine)(4.32g,12mmole)與9,9'-螺二芴-2-基硼酸(Spiro-9,9'-bifluorene-2-boronic acid)(4.78g,10mmole)及碳酸鉀(6.73g,35mmole)置於反應瓶,再加入34毫升的甲苯、10毫升的乙醇、14毫升的去離子水,使反應瓶置於油浴中,並連接氮氣及冷凝管後,開啟加熱攪拌80℃,同時,加入四(三苯基膦)鈀(Pd(PPh3)4)(0.58g,0.5mmole)於反應瓶。待反應完全且有固體析出時,移除油浴,使其降溫後進行過濾,使濾得的濾餅再加入100毫升的去離子水,經攪拌10分鐘後進行再過濾,並再將濾得的濾餅加入250毫升的四氫呋喃,經加熱攪拌直至全溶後,加入一含有20克氧化矽之管柱進行層析純化,並濃縮至白色固體析出,再經乙酸乙酯沖洗、過濾及乾燥後,獲得白色固體(約5.9g),產率82.69%。
1H NMR(CDCl3,400MHz),δ8.64(d,2H),8.50(t,1H),8.42(d,2H),8.18(t,1H),8.14(d,1H),8.09(s,1H),7.95(d,1H),7.85-7.89(m,4H),7.78(t,1H),7.72-7.74(m,2H),7.65(t,1H),7.53(t,2H),7.35-7.44(m,7H),7.13-7.17(m,3H),6.85(d,1H),6.77-6.82(m,3H),2.47(s,3H).
合成例4:化合物3-4之合成
將4-聯苯-3-基-6-(3-溴苯基)-2-(吡啶-3-基)-嘧啶(4-([1,1'-biphenyl]-3-yl)-6-(3-bromophenyl)-2-(pyridin-3-yl)pyrimidine)(10g,21.53mmole)與9,9'-螺二芴-2-基硼酸(9,9'-spirobi[fluoren]-2-ylboronic acid)(8.14g,22.61mmole)置於反應槽,再加入120毫升的甲苯。將碳酸鉀(10.41g,75.37mmole)溶於70毫升的去離子水後加入反應槽,同時,加入四(三苯基膦)鈀(Pd(PPh3)4)(1.24g,1.077mmole)及30毫升的乙醇,開啟加熱攪拌,加熱直至80℃並反應隔夜。待反應完成後加入300毫升的去離子水,經攪拌30分鐘後停止攪拌並靜置使其分層,進行萃取,將萃取後濾液加入以矽膠填充的管柱進行層析法純化,濃縮至濃稠態後再加入300毫升的己烷加強析出,有機層合併過濾固體,得乳白色固體(約7克)即為產物。
1H NMR(CDCl3,400MHz),δ 9.90(d,1H),8.96(td,1H),8.76(dd,1H),8.47(s,1H),8.35(s,1H),8.21(d,1H),8.14(d,1H),8.03(s,1H),7.99(d,1H),7.91(d,1H),7.86(d,2H),7.74-7.79(m,2H),7.71(d,2H),7.64(t,1H),7.58(d,1H),7.36-7.54(m,8H),7.12-7.16(m,3H),7.04(d,1H),6.82(d,2H),6.77(d,1H).
合成例5:化合物3-6之合成
將4-聯苯-3-基-6-(3-溴苯基)-2-(吡啶-3-基)-嘧啶(4-([1,1'-biphenyl]-3-yl)-6-(3-bromophenyl)-2-(pyridin-3-yl)pyrimidine)(10g,21.53mmole)與9,9'-螺二芴-2-基硼酸(Spiro-9,9'-bifluorene-2-boronic acid)(9.41g,22.61mmole)置於反應槽,加入120毫升的甲苯。將碳酸鉀(10.41g,75.37mmole)溶於70毫升的去離子水後加入反應槽,同時,加入四(三苯基膦)鈀(Pd(PPh3)4)(1.24g,1.077mmole)及30毫升的乙醇,開啟加熱及攪拌,加熱直至80℃並反應隔夜。待反應完成後加入300毫升的去離子水,經攪拌30分鐘後停止攪拌並靜置使其分層,進行萃取,將萃取後濾液加入以矽膠填充的管柱進行層析法純化,濃縮至濃稠態後再加入300毫升的己烷加強析出,有機層合併過濾固體,得乳白色固體(約6克)。
1H NMR(CDCl3,400MHz),δ 9.97(d,1H),8.97(td,1H),8.77(dd,1H),8.55(s,1H),8.52(t,1H),8.24-8.29(m,2H),8.15(s,2H),7.97(d,1H),7.90(d,2H),7.84(d,1H),7.79(d,1H),7.72(d,2H),7.64-7.69(m,2H),7.52(t,2H),7.40-7.48(m,5H),7.17(t,3H),6.88(d,1H),6.84(d,2H),6.80(d,1H).
合成例6:化合物3-7之合成
將4-聯苯-3-基-6-(4-溴苯基)-2-(吡啶-3-基)-嘧啶(4-[1,1’-biphenyl]-3-yl-6-(4-bromophenyl)-2-(pyridine-3-yl)pyrimidine)(9.28g,20mmole)與9,9'-螺二芴-3-基硼酸(9,9’-spirobifluorene-3-yl boronic acid)(9.3g,24mmole)、四(三苯基磷)鈀(Pd(PPh3)4)(1.16g,1mmole)與碳酸鉀(5.5g,40mmole)置入於1000毫升的雙頸圓底反應瓶中,分別加入320毫升的甲苯、220毫升的乙醇和100毫升的去離子水,使反應瓶置於油浴中,並連接氮氣及冷凝管後,開啟加熱攪拌80℃。待反應完全且有固體析出時,移除油浴,使其降溫後進行過濾,使濾得的固體再以300毫升的丙酮沖洗、乾燥,獲得白色固體(約8.9克),產率64%。
1H NMR(CDCl3,400MHz)δ 9.96(s,1H),8.99(td,1H),8.77(dd,1H),8.52(t,1H),8.42(d,2H),8.27(d,1H),8.17(s,1H),8.14(d,1H),7.96(d,1H),7.88(d,4H),7.80(d,1H),7.73(dd,2H),7.67(t,1H),7.53(t,2H),7.45-7.51(m,1H),7.38-7.44(m,5H),7.13-7.16(m,3H),6.86(s,1H),6.81(d,2H),6.78(d,1H).
合成例7:化合物3-8之合成
將4-聯苯-3-基-6-(4-溴苯基)-2-(吡啶-3-基)-嘧啶(4-([1,1'-biphenyl]-3-yl)-6-(4-bromophenyl)-2-(pyridin-3-yl)pyrimidine),(9.28g,20mmole)、9-菲硼酸(phenanthrene-9-yl-9-boronic acid)(5.3g,24mmole)、四(三苯基磷)鈀(Pd(PPh3)4)(1.16g,1mmole)與碳酸鉀(5.5g,40mmole)置入於1000毫升的雙頸圓底反應瓶中,分別加入320毫升的甲苯、220毫升的乙醇和100毫升的去離子水,使反應瓶置於油浴中,並連接氮氣及冷凝管後,開啟加熱攪拌80℃。待反應完全且有固體析出時,移除油浴,使其降溫後進行過濾、烘乾後,獲得灰黑色固體(約5.4克),產率48%。
1H NMR(CDCl3,400MHz)δ9.98(d,1H),9.01(td,1H),8.82(d,1H),8.78(d,1H),8.76(d,1H),8.55(s,1H),8.46(d,2H),8.30(dd,1H),8.23(s,1H),7.90(d,1H),7.95(d,1H),7.77-7.82(m,3H),7.65-7.64(m,3H),7.66-7.78(m,7H),7.58(t,1H),7.52(t,2H),7.50(d,1H),7.49(d,1H),7.44(t,1H).
合成例8:化合物1-2之合成
將1-聯苯-3-基-3-(4-溴苯基)-丙烯酮(1-Biphenyl-3-yl-3-(4-bromo-phenyl)-propenone)(36.7g,101.14mmole)、4-氟基苯甲脒鹽酸鹽(4-Fluorobenzamidinehydrochloride)(17.66g,101.14mmole)與氫氧化鈉(5.78g,144.5mmole)及200毫升的乙醇置於反應瓶內,開啟加熱直至75℃並反應隔夜。待反應完成後進行過濾,獲得乳白色固體(約23克)。
將4-聯苯-3-基-6-(4-溴苯基)-2-(4-氟苯基)-嘧啶(4-([1,1'-biphenyl]-3-yl)-6-(4-bromophenyl)-2-(4-fluorophenyl)pyrimidine)(10g,20.77mmole)與9,9'-螺二芴-2-基硼酸(9,9'-spirobi[fluoren]-2-ylboronic acid)(7.85g,21.8mmole)置於反應槽,加入120毫升的甲苯。將碳酸鉀(10g,72.7
mmole)溶於70毫升的去離子水後加入反應槽,同時,加入四(三苯基膦)鈀(Pd(PPh3)4)(1.2g,1.039mmole)及30毫升的乙醇,開啟加熱及攪拌,加熱直至80℃並反應隔夜。待反應完成後,加入300毫升的去離子水,經攪拌30分鐘後停止攪拌並靜置使其分層,進行萃取,加入以矽膠填充的管柱進行層析法純化,濃縮至濃稠態加入300毫升的己烷加強析出,過濾固體,獲得乳白色固體(約6克)。
1H NMR(CDCl3,400MHz)δ 8.69-8.72(m,2H),8.44(t,1H),8.23(d,2H),8.20(d,1H),8.00(s,1H),7.96(d,1H),7.87-7.90(m,3H),7.75(d,1H),7.69-7.73(m,3H),7.61-7.64(m,3H),7.50(t,2H),7.38-7.43(m,4H),7.19(t,2H),7.14(t,3H),7.04(d,1H),6.81(d,2H),6.75(d,1H)
將上述材料與化合物EET09的物性值表示於表2中,其中,該化合物EET09如日本專利第2011003793A號所述。
各物性值之測定方法如下所示。
(1)熱裂解溫度(Td)
使用熱重分析儀(Perkin Elmer,TGA 8000)進行量測,在常壓且具氮氣氣氛下,以20℃/分鐘的程序升溫速率,對製得的化合物的熱裂解性質進行量測,並將重量減小至起始重量的95%的溫度即為熱裂解溫度(Td)。
(2)玻璃轉移溫度(Tg)
使用示差掃描熱分析儀(DSC;Perkin Elmer,DSC 8000)以20℃/分鐘的程序升溫速率對製得的化合物進行量測。
(3)最高佔據分子軌道(HOMO)之能階值
另外,將化合物製成薄膜狀態,於大氣下使用光電子分光光度計(Riken Keiki,Surface Analyzer)量測其電離電位數值,將其數值進一步轉化後即為HOMO能階值。
(4)最低未占分子軌道(LUMO)之能階值
將上述化合物之薄膜以UV/VIS分光光度計(Perkin Elmer,Lambda 20)量測其吸收波長之邊界值,將該值經轉換得能隙值,使能隙值與HOMO能階的數值相加,即得LUMO能階。
(5)三重態能量值(ET)
使用螢光光譜儀(Perkin Elmer,LS 55)於溫度77K下量測發光光譜,再經由計算,可得ET。
製備實施例1-1:有機電激發光元件之製造
於基底載入蒸鍍系統使用前,先以溶劑及紫外線臭氧清洗基底進行脫脂。之後,將基底傳送至真空沉積室,於基底之頂部沉積所有層。依第2圖所示之各層係由加熱的
蒸鍍舟(boat)在約10-6托之真空度依序沉積:a)電洞注入層,厚度20奈米,包含摻雜有6%重量比之p型電性傳導摻質之HTM,其中該p型電性傳導摻質係購自上海瀚豐化工有限公司,且HTM係購自Merck & Co.,Inc.;b)電洞傳輸層,厚度150奈米,HTM;c)激子阻擋層,厚度10奈米,HT(昱鐳光電製備);d)發光層,厚度25奈米,包含摻雜有4%重量比BD之EBH,其中,BD及EBH為昱鐳光電製備;e)電子傳輸層,厚度20奈米,包含化合物2-4及摻雜之喹啉鋰(Liq),重量比為5:5;f)電子注入層,厚度1.5奈米,Liq;及g)陰極,厚度約180奈米,包含鋁(Al)。
元件結構可表示如:ITO/HTM:p型電性傳導摻質(20奈米)/HTM(150奈米)/HT(10奈米)/EBH:BD(25奈米)/化合物2-4:Liq(20奈米)/Liq(1.5奈米)/Al(180奈米)。
於沉積形成上述各層後,該元件自沉積室傳送至乾燥箱中,隨即以UV可固化環氧樹脂及含有吸濕劑之玻璃蓋板進行封裝。該有機電激發光元件具有9平方毫米之發光區域。
製備實施例1-2至1-5:有機電激發光元件之製造
除將製備實施例1-1中電子傳輸層之化合物2-4各別置換為化合物3-4、3-7、3-8及3-6,係根據製備實施例1-1
之層結構製備實施例1-2、製備實施例1-3、製備實施例1-4及製備實施例1-5。
製備實施例1-1A至1-1C:有機電激發光元件之製造
除了異動製備實施例1-1中電子傳輸層之化合物2-4及摻雜之喹啉鋰(Liq)的重量比分別為1:0、7:3及3:7,係根據製備實施例1-1之層結構製備實施例1-1A、製備實施例1-1B及製備實施例1-1C。
製備實施例1-3A至1-3C:有機電激發光元件之製造
除了異動製備實施例1-3中電子傳輸層之化合物3-7及摻雜之喹啉鋰(Liq)的重量比分別為1:0、7:3及3:7,製備實施例1-3A、製備實施例1-3B及製備實施例1-3C係如製備實施例1-3之層結構。
製備實施例1-4A:有機電激發光元件之製造
除了異動製備實施例1-4中電子傳輸層之化合物3-8及摻雜之喹啉鋰(Liq)的重量比分別為7:3,製備實施例1-4A係如製備實施例1-4之層結構。
製備實施例1-5A:有機電激發光元件之製造
除了異動製備實施例1-5中電子傳輸層之化合物3-6及摻雜之喹啉鋰(Liq)的重量比分別為7:3,製備實施例1-5A係如製備實施例1-5之層結構。
比較製備實施例1:有機電激發光元件之製造
將有機電激發光元件製造成結構類似製備實施例1-1的層結構,除了將製備實施例1-1中電子傳輸層之化合物2-4置換為化合物EET09。其中,該化合物EET09如日本
專利第2011003793A號所述。
比較製備實施例2:有機電激發光元件之製造
將有機電激發光元件製造成結構類似製備實施例1-1的層結構,除了將製備實施例1-1中電子傳輸層之化合物2-4置換為化合物ETM801。其中,該化合物ETM801如日本專利第6367389號所述,並由昱鐳光電製備。
試驗實施例1至4:
將上述製備實施例1-1至1-4製成之有機電激發光元件之電激發光性質均使用定電流源(KEITHLEY 2400 Source Meter,made by Keithley Instruments,Inc.,Cleveland,Ohio)及光度計(PHOTO RESEARCH SpectraScan PR 650,made by Photo Research,Inc.,Chatsworth,Calif.)於室溫下測量其發光性質,將其驅動電壓(Vd)、發光效率及於電流密度50J下之LT95之值列示於表3,其中,LT95值之定義為亮度水平降至相對於初始亮度的95%的水平所消耗的時間,係作為評估有機電激發光元件之使用壽命或穩定性的衡量標準。
比較試驗實施例1:
測量比較製備實施例1製成之有機電激發光元件之電激發光性質,其測量方式與試驗實施例1相同。
試驗實施例5:
將上述製備實施例1-3製成之有機電激發光元件,使用定電流源(KEITHLEY 2400 Source Meter,made by Keithley Instruments,Inc.,Cleveland,Ohio)及光度計(PHOTO
RESEARCH SpectraScan PR 650,made by Photo Research,Inc.,Chatsworth,Calif.)於電流密度10毫安培/平方釐米(mA/cm2)下量測其電激發光性質,包括:驅動電壓(Vd)、發光效率、色座標CIE(x,y)及藍光指數(blue index)之值,並記錄於表4。其中,該藍光指數係發光效率及色座標y的比值,藍光指數愈高,顯示該元件之效率愈佳。
試驗實施例6:
以同試驗實施例5之測量方法,測量製備實施例1-3製成之有機電激發光元件之電激發光性質,惟異動其電流密度為50毫安培/平方釐米(mA/cm2)。
比較試驗實施例2、3:
將比較製備實施例2製成之有機電激發光元件,以試驗實施例5之測量方法,分別量測於電流密度10及50毫安培/平方釐米(mA/cm2)下其電激發光性質。
試驗實施例7至18:
針對電子傳輸層之不同摻雜比例,列出製備實施例1-1、1-3、1-4及1-6之有機電激發光元件的測量值,並記錄於表5。
製備實施例2-1:有機電激發光元件之製造
於基底載入蒸鍍系統使用前,先以溶劑及紫外線臭氧清洗基底進行脫脂。之後,將基底傳送至真空沉積室,於基底之頂部沉積所有層。依第3圖所示之各層係由加熱的蒸鍍舟(boat)在約10-6托之真空度依序沉積:a)電洞注入層,厚度20奈米,包含摻雜有6%重量比之p型電性傳導摻質之HTM,其中該p型電性傳導摻質係購自上海瀚豐化工有限公司,且HTM係購自Merck & Co.,Inc.;b)電洞傳輸層,厚度150奈米,HTM;c)激子阻擋層,厚度10奈米,HT(昱鐳光電製備);
d)發光層,厚度25奈米,包含摻雜有4%重量比BD之EBH,其中,BD及EBH為昱鐳光電製備;e)電洞阻擋層,厚度5奈米,化合物2-4;f)電子傳輸層,厚度20奈米,包含化合物2-4及摻雜之喹啉鋰(Liq),重量比為5:5;g)電子注入層,厚度1.5奈米,Liq;及h)陰極,厚度約180奈米,包含鋁(Al)。
元件結構可表示如:ITO/HTM:p型電性傳導摻質(20奈米)/HTM(150奈米)/HT(10奈米)/EBH:BD(25奈米)/化合物2-4(5奈米)/化合物2-4:Liq(20奈米)/Liq(1.5奈米)/Al(180奈米)。
於沉積形成上述各層後,該元件自沉積室傳送至乾燥箱中,隨即以UV可固化環氧樹脂及含有吸濕劑之玻璃蓋板進行封裝。該有機電激發光元件具有9平方毫米之發光區域。
製備實施例2-2:有機電激發光元件之製造
除將製備實施例2-1中電洞阻擋層及電子傳輸層之化合物2-4置換為化合物3-7,製備實施例2-2係如製備實施例1-1之層結構。
製備實施例2-1A至2-1B:有機電激發光元件之製造
除了異動製備實施例2-1中電子傳輸層之化合物2-4及摻雜之喹啉鋰(Liq)的重量比分別為7:3及3:7,製備實施例2-1A及製備實施例2-1B係如製備實施例2-1之層結構。
製備實施例2-2A至2-2B:有機電激發光元件之製造
除了異動製備實施例2-2中電子傳輸層之化合物3-7及摻雜之喹啉鋰(Liq)的重量比分別為7:3及3:7,製備實施例2-2A及製備實施例2-2B係如製備實施例2-2之層結構。
比較製備實施例3:有機電激發光元件之製造
將有機電激發光元件製造成結構類似製備實施例2-1的層結構,除了將製備實施例2-1中電洞阻擋層及電子傳輸層之化合物2-4各別置換為化合物EET09。
試驗實施例19至24:
以相同試驗實施例7之量測方法,量測上述製備實施例2-1至2-2製成之有機電激發光元件之電激發光性質,並記錄於表6。
比較試驗實施例4:
以相同試驗實施例19之量測方法,量測比較製備實施例4製成之有機電激發光元件之電激發光性質,並記錄於表6。
如上所述,可見包含本發明之具式(I)結構之苯基聯苯嘧啶類化合物之有機電激發光元件展現良好耐熱性並顯著
改善其使用壽命,因此,本發明之有機電激發光元件能符合多樣的應用需求,具有極高之技術價值。
上述實施例僅為例示性說明,而非用於限制本發明。任何熟習此項技藝之人士均可在不違背本發明之精神及範疇下,對上述實施例進行修飾與改變。因此,本發明之權利保護範圍係由本發明所附之申請專利範圍所定義,只要不影響本發明之效果及實施目的,應涵蓋於此公開技術內容中。
200‧‧‧有機電激發光元件
210‧‧‧基板
220‧‧‧陽極
230‧‧‧電洞注入層
240‧‧‧電洞傳輸層
245‧‧‧電子阻擋層
250‧‧‧發光層
260‧‧‧電子傳輸層
270‧‧‧電子注入層
280‧‧‧陰極
Claims (13)
- 如申請專利範圍第1項所述之具式(I)結構之苯基聯苯嘧啶類化合物,其中,X1係選自由未經取代之吡啶基、經鹵素取代之苯基及經C1-4烷基取代之苯基所組成群組中之一者。
- 如申請專利範圍第1項所述之具式(I)結構之苯基聯苯嘧啶類化合物,其中,A1為經取代或未經取代之C9-30稠合多環芳香烴基(fused polycyclic aromatic)、具有螺狀結構之經取代或未經取代之C9-30芳香烴基或經取代或未經取代之含有選自由N、O、及S所組成群組中之至少一雜原子之C5-30稠合多環芳香烴基。
- 一種有機電激發光元件,包含:陰極;陽極;以及有機層,係介於該陰極與陽極之間,且該有機層包含如申請專利範圍第1項所述之具式(I)結構之苯基聯苯嘧啶類化合物。
- 如申請專利範圍第9項所述之有機電激發光元件,其中,該有機層係電子傳輸層,且其厚度係20奈米至30奈米。
- 如申請專利範圍第10項所述之有機電激發光元件,其中,該電子傳輸層復包含N型電性傳導摻質,且該N型電性傳導摻質的含量為大於0重量%至50重量%。
- 如申請專利範圍第11項所述之有機電激發光元件,其中,該N型電性傳導摻質為喹啉鋰。
- 如申請專利範圍第10項所述之有機電激發光元件,其中,該有機層復包括電洞阻擋層,且其厚度係大於0奈米至5奈米。
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2018
- 2018-10-23 TW TW107137368A patent/TWI692471B/zh active
- 2018-10-31 CN CN201811290088.XA patent/CN111087349A/zh active Pending
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US11393983B2 (en) | 2022-07-19 |
US20200127211A1 (en) | 2020-04-23 |
TWI692471B (zh) | 2020-05-01 |
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