TWI752665B - 一種咪唑並吡啶的芳胺類化合物及其應用 - Google Patents
一種咪唑並吡啶的芳胺類化合物及其應用 Download PDFInfo
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Abstract
本發明涉及一種咪唑並吡啶的芳胺類化合物及其應用。所述化合物具有式(I)結構。本發明化合物具有昇華溫度低,熱穩定性好,折射率高、可見光區折射率差異小等優點,可做為光提取層材料,應用於有機發光器件中。
Description
本發明涉及有機電致發光材料領域,特別涉及咪唑並吡啶的芳胺類化合物及其在有機電致發光器件上的應用。
目前,作為新一代顯示技術的有機電致發光器件(OLED)在顯示和照明技術方面都獲得了越來越多的關注,應用前景十分廣泛。但是,和市場應用要求相比,OLED器件的發光效率、驅動電壓、使用壽命等性能還需要繼續加強和改進。
一般來說,OLED器件基本結構為在金屬電極中間夾雜各種不同功能的有機功能材料薄膜,猶如一個三明治的結構,在電流的驅動下,從陰陽兩極分別注入空穴和電子,空穴和電子在移動一段距離後,在發光層得到複合,並以光或熱的形式進行釋放,從而產生了OLED的發光。然而,有機功能材料是有機電致發光器件的核心組成部分,材料的熱穩定性、光化學穩定性、電化學穩定性、量子產率、成膜穩定性、結晶性、色飽和度等都是影響器件性能表現的主要因素。
一方面,如何縮小OLED器件內外量子效率之間的巨大差距,如何減少器件中的全發射效應、提高光耦合提取比例引起人們的廣泛關注。現行的光提取層的材料的折射率都比較低,尤其是在紅光波段,通常折射率小於1.85,極少數大於1.90,更少數大於2.0。另外,現有的光提取材料在紅綠藍光波段區域的折射率差別較大,造成三種顏色光的最佳厚度差別大,未能充分體現光提取材料的性能。對於頂發射器件來說,光提取層材料的折射率越大,相應的外量子效率就越高,器件的發光效率就越高。所以,開發高折射率的光提取層材料尤為重要。CN103828485和TW201506128公開了以多聯苯二胺為核心的光提取層材料,但是折射率還是稍微偏低,尤其是在紅光方面更需要進一步提升。
針對上述領域中的缺陷,本發明提供一種咪唑並吡啶的芳胺類化合物,該類化合物具有昇華溫度低,熱穩定性好,折射率高、可見光區折射率差異小等優點,可用於有機發光器件中。
一種咪唑並吡啶的芳胺類化合物,其結構式為式I所示:(I)
其中n為1或2;
X1、X2、X3、X4獨立的表示為CR0
或者N,R0
獨立的選自氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、芳烷基、氨基、矽烷基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的雜芳基、腈、異腈,且相鄰的R0
能鍵接成並環;
其中R1
為單鍵、C1-C30亞烷基、C1-C30亞雜烷基、C3-C30亞環烷基、取代或未取代的C6-C30的亞芳基、取代或未取代的C2-C28的亞雜芳基;
其中R2獨立的選自氫、氘、鹵素、C1-C30烷基、C1-C30雜烷基、C3-C30環烷基、C1-C30烷氧基、C6-C60芳氧基、氨基、矽烷基、腈基、異腈基、膦基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的雜芳基;
其中Ar1
為取代或未取代的C6-C60的芳基、取代或未取代的C6-C60的雜芳基、經取代或未經取代C3-C60環烷基、取代或未取代的C6-C60的芳胺基;
其中B為取代或未取代的C6-C60的芳基或亞芳基、取代或未取代的C6-C60的雜芳基或亞雜芳基、經取代或未經取代的C3-C60環烷基或亞環烷基、取代或未取代的C6-C60的芳胺基或亞芳胺基;
其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Se、Si、Ge中的至少一個雜原子替換;所述取代為被氘、鹵素、C1-C30烷基、苯基、萘基或聯苯基取代。
優選:其結構式如式II所示(II)
其中R1
為單鍵、C1-C10亞烷基、C1-C10亞雜烷基、C3-C10亞環烷基、取代或未取代的C6-C30的亞芳基、取代或未取代的C2-C28的亞雜芳基;
其中R2獨立的選自氫、氘、鹵素、C1-C10烷基、C1-C10雜烷基、C1-C10烷氧基、C3-C30環烷基、C6-C30芳氧基、氨基、矽烷基、腈、異腈、膦基、取代或未取代的C6-C30的芳基、取代或未取代的C1-C30的雜芳基;
其中Ar1
、Ar2
為取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的雜芳基、經取代或未經取代的單環或多環C3-C30脂肪族環或芳香族環、取代或未取代的C6-C30的芳胺基;
其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Si中的至少一個雜原子替換;所述取代為被氘、鹵素、C1-C8烷基、苯基、萘基或聯苯基取代。
優選:其中R1
為C1-C8烷基取代或未取代的C6-C20的亞芳基、C1-C8烷基取代或未取代的C2-C18的亞雜芳基;其中R2
為C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的雜芳基;其中Ar1
、Ar2
為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環、取代或未取代的C6-C20的芳胺基;其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換;所述取代為被氘、C1-C8烷基、苯基、萘基或聯苯基取代。
更優選:其中R1
為C1-C4烷基取代或未取代的C6-C10的亞芳基、C1-C4烷基取代或未取代的C2-C8的亞雜芳基;其中Ar1
、R2
為C1-C4烷基取代或未取代的C6-C10的芳基、C1-C4烷基取代或未取代的C1-C8的雜芳基;其中Ar2
為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環、取代或未取代的C6-C20的芳胺基;其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換;所述取代為被氘、C1-C4烷基、苯基、萘基或聯苯基取代。
作為優選的化合物,Ar1或Ar2至少之一含有以下結構式(III),其中R1
為單鍵、C1-C8亞烷基、C1-C8亞雜烷基、C3-C8亞環烷基、C1-C8烷基取代或未取代的C6-C30的亞芳基、C1-C8烷基取代或未取代的C2-C28的亞雜芳基;其中R2
為氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、C3-C8環烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的雜芳基。(III)
作為優選的化合物,可為以下式(IV)結構,其中R1
為單鍵、C1-C8亞烷基、C1-C8亞雜烷基、C3-C8亞環烷基、C1-C8烷基取代或未取代的C6-C30的亞芳基、C1-C8烷基取代或未取代的C2-C28的亞雜芳基;其中R2
為氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、C3-C8環烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的雜芳基;其中Ar1
為取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的雜芳基、經取代或未經取代的單環或多環C3-C30脂肪族環或芳香族環,A為取代或未取代的C6-C30的亞芳基、取代或未取代的C6-C30的亞雜芳基;其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Si中的至少一個雜原子替換;所述取代為被氘、鹵素、C1-C8烷基、苯基、萘基或聯苯基取代。(IV)
優選:其中R1
為C1-C8烷基取代或未取代的C6-C20的亞芳基、C1-C8烷基取代或未取代的C2-C18的亞雜芳基;其中R2
為C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的雜芳基;其中Ar1
為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環,A為取代或未取代的C6-C20的亞芳基、取代或未取代的C6-C20的亞雜芳基;其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換;所述取代為被氘、C1-C8烷基、苯基、萘基或聯苯基取代。
優選:X1、X2、X3、X4獨立的表示為CR0
,R0
獨立的選自氫、C1-C8烷基。
作為優選的化合物為以下化合物:
A 1 | A 2 | A 3 |
A 4 | A 5 | A 6 |
A 7 | A 8 | A 9 |
A 10 | A 11 | A 12 |
A 13 | A 14 | A 15 |
A 16 | A 17 | A 18 |
A 19 | A 20 | A 21 |
A 22 | A 23 | A 24 |
A 25 | A 26 | A 27 |
A 28 | A 29 | A 30 |
A 31 | A 32 | A 33 |
A 34 | A 35 | A 36 |
A 37 | A 38 | A 39 |
A 40 | A 41 | A 42 |
A 43 | A 44 | A 45 |
A 46 | A 47 | A 48 |
A 49 | A 50 | A 51 |
A 52 | A 53 | A 54 |
A 55 | A 56 | A 57 |
A 58 | A 59 | A 60 |
A 61 | A 62 | A 63 |
A 64 | A 65 | A 66 |
A 67 | A 68 | A 69 |
A 70 | A 71 | A 72 |
A 73 | A 74 | A 75 |
A 76 | A 77 | A 78 |
A 79 | A 80 | A 81 |
A 82 | A 83 | A 84 |
作為優選的化合物為以下化合物:
B 1 | B 2 | B 3 |
B 4 | B 5 | B 6 |
B 7 | B 8 | B 9 |
B 10 | B 11 | B 12 |
B 13 | B 14 | B 15 |
B 16 | B 17 | B 18 |
B 19 | B 20 | B 21 |
B 22 | B 23 | B 24 |
B 25 | B 26 | B 27 |
B 28 | B 29 | B 30 |
B 31 | B 32 | B 33 |
B 34 | B 35 | B 36 |
B 37 | B 38 | B 39 |
B 40 | B 41 | B 42 |
B 43 | B 44 | B 45 |
B 46 | B 47 | B 48 |
B 49 | B 50 | B 51 |
B 52 | B 53 | B 54 |
B 55 | B 56 | B 57 |
B 58 | B 59 | B 60 |
B 61 | B 62 | B 63 |
B 64 | B 65 | B 66 |
B 67 | B 68 | B 69 |
B 70 | B 71 | B 72 |
B 73 | B 74 | B 75 |
B 76 | B 77 | B 78 |
B 79 | B 80 | B 81 |
B 82 | B 83 | B 84 |
B 85 | B 86 | B 87 |
B 88 | B 89 | B 90 |
B 91 | B 92 | B 93 |
B 94 | B 95 | B 96 |
B 97 | B 98 | B 99 |
B 100 | B 101 | B 102 |
B 103 | B 104 | B 105 |
B 106 | B 107 | B 108 |
B 109 | B 110 | B 111 |
B 112 | B 113 | B 114 |
B 115 | B 116 | B 117 |
B 118 | B 119 | B 120 |
B 121 | B 122 | B 123 |
B 124 | B 125 | B 126 |
B 127 | B 128 | B 129 |
B 130 | B 131 | B 132 |
B 133 | B 134 | B 135 |
B 136 | B 137 | B 138 |
B 139 | B 140 | B 141 |
B 142 | B 143 | B 144 |
B 145 | B 146 | B 147 |
B 148 | B 149 | B 150 |
B 151 | B 152 | B 153 |
B 154 | B 155 | B 156 |
B 157 | B 158 | B 159 |
B 160 | B 161 | B 162 |
B 163 | B 164 | B 165 |
B 166 | B 167 | B 168 |
B 169 | B 170 | B 171 |
B 172 | B 173 | B 174 |
B 175 | B 176 | B 177 |
B 178 | B 179 | B 180 |
B 181 | B 182 | B 183 |
B 184 | B 185 | B 186 |
B 187 | B 188 | B 189 |
B 190 | B 191 | B 192 |
B 193 | B 194 | B 195 |
B 196 | B 197 | B 198 |
所述應用為化合物作為OLED器件的光提取層材料。
本發明的咪唑並吡啶的芳胺類化合物材料具有昇華溫度低,熱穩定性好,發光效率高,折射率高、可見光區折射率差異小等優點,可用於有機發光器件中。作為光提取層材料,該器件具有發光效率高、長時間熱穩定性好的優點,具有應用於AMOLED產業的可能。
下述實施例僅為了便於理解技術發明,不應視為本發明的具體限製。
本發明中的化合物合成中涉及的原物料和溶劑等均購自於Alfa、Acros等本領域技術人員熟知的供應商。
化合物03的合成:向一個2L三口瓶,依次將化合物01(80g,256.4mmol,1.0eq)、化合物02(71.64g,769.2mmol,3.0eq),t-BuONa(49.2g,512.8mmol,2.0eq)、Pd2
(dba)3
(2.35g,2.56mmol,0.01eq), X-phos(2.44g,5.13mmol,0.02eq),分子篩乾燥的甲苯(800ml)投入到燒瓶中,真空、氮氣置換3次,油浴加熱到108度左右,保溫攪拌回流2h,取樣點板01原料反應完。反應液降溫至80℃,滴加甲醇(800ml)攪拌1h,降至室溫後抽濾,得到固體加入THF(900ml)和正己烷(600ml)熱打漿2h,抽濾,烘乾得到71.5g類白色固體,收率82.8%。質譜:337.4(M+H)。
化合物06的合成:向一個2L單口瓶,依次將化合物04(76g,214.6mmol,1.0eq)、化合物05(50.5g,536.6mmol,2.5q),NaHCO3
(27.05g,322mmol,1.5eq)、異丙醇(700ml)投入到燒瓶中,油浴加熱到80度左右,保溫攪拌回流7h,取樣點板原料反應完。降溫,滴加去離子水,攪拌2h左右,抽濾。固體用乙酸乙酯打漿,抽濾烘乾。得到54.5g白色固體化合物06,收率72.7%。質譜:349.2(M+H)。
化合物A1的合成:向一個2L三口瓶,依次將化合物06(45.7,130.8mmol,2.2eq)、化合物03(20g,59.4mmol,1eq),t-BuONa(17.1g,178.3mmol,3.0eq)、Pd2
(dba)3
(1.09g,1.19mmol,0.02eq), X-phos(1.13g,2.38mmol,0.04eq),分子篩乾燥的甲苯(600ml)投入到燒瓶中,真空、氮氣置換3次,油浴加熱到108度左右,保溫攪拌回流16h,取樣點板06原料反應完。反應液降溫至80℃,滴加正己烷(800ml)攪拌1h,降至室溫後抽濾,得到固體加入二氯甲烷(1.6L)溶解完全,去離子水洗四次(500ml*4),分液後有機相用矽膠過濾,少量二氯甲烷沖洗矽膠,濃縮有機相得到固體,採用四氫呋喃/甲醇(250ml/300ml)進行重結晶2次,烘乾得到32g淡黃色固體,收率61.6%。得到的合成品經過昇華純化得到21.2克淡黃色固體化合物A1,收率66.2%。質譜:874.1(M+H)。1
HNMR(400MHz,CDCl3
)δ8.01(d,J=6.8Hz,2H),7.72(d,J=8.0Hz,3H),7.64(d,J=9.0Hz, 2H), 7.51(d,J=8.3Hz ,4H), 7.40–7.13(m,23H), 7.10(d,J=7.2Hz, 2H), 6.74(d,J=6.8Hz, 2H)。
化合物08的合成:選取對應的材料,參照化合物03的合成方式和處理方法,只需要將對應的原物料變更即可。質譜:412.5(M+H)。
化合物A16的合成:選取對應的材料,參照化合物A1的合成、昇華得到黃色固體化合物A16。質譜:949.1(M+H)。1
HNMR(400MHz,CDCl3
)δ8.48(d,2H),7.73(dd,4H),7.58–7.44(m,12H), 7.37(m, 8H), 7.33–7.17(m,14H), 7.08(d,4H), 7.00(d,2H),6.86(d,2H)。
化合物10的合成:選取對應的材料,參照化合物03的合成方式和處理方法,只需要將對應的原物料變更即可。質譜:377.5(M+H)
化合物A17的合成:選取對應的材料,參照化合物A1的合成、昇華得到黃色固體化合物A17。質譜:913.1(M+H)。1
HNMR (400MHz,CDCl3
)δ8.48(d,2H), 7.86(d,2H), 7.73(dd,4H), 7.49(dd, J=14.4,9.4Hz,10H),7.37(m,4H),7.25(dd,J=28.1,8.1Hz,12H),7.08(m,4H),7.00(d,2H),6.86(d,2H),1.69(s,6H)。
化合物12的合成:選取對應的材料,參照化合物06的合成方式和處理方法,只需要將對應的原物料變更即可。質譜:349.03(M+H)。
化合物A22的合成:選取對應的材料,參照化合物A1的合成、昇華得到黃色固體化合物A22。質譜:873.1(M+H)。1
HNMR(400MHz,CDCl3
)δ8.48(d,2H),7.73(dd,4H),7.60–7.42(m,12H), 7.37(m, 8H),7.33–7.16(m,10H),7.04(d,J=40.0Hz,6H),6.86(d,2H)
化合物14的合成:選取對應的材料,參照化合物06的合成方式和處理方法,只需要將對應的原物料變更即可。質譜:397.30(M+H)。
化合物15的合成:選取對應的材料,參照化合物03的合成方式和處理方法,只需要將對應的原物料變更即可。質譜:361.4(M+H)。
化合物17的合成:向一個2L三口瓶,依次將化合物15(45g,124.5mmol,1.0eq)、化合物16(36.98g,130.7mmol,1.05eq),CuI(2.37g,12.45mmol,2eq)、1,10-菲羅啉(4.49g,24.9mmol,0.2eq),K2
CO3
(34.41g,2.49mmol,0.04eq),DMF(450ml)投入到燒瓶中,真空、氮氣置換3次,油浴加熱到120度左右,保溫攪拌8h,取樣點板15原料反應完。反應液降溫至40℃,滴加去離子水(800ml)攪拌1h,降至室溫後過濾,得到固體加入甲苯(400ml)溶解完全,去離子水洗(100ml*3),分液後有機相用矽膠過濾,少量甲苯沖洗矽膠,濃縮有機相至剩餘250ml,再滴加甲醇(300ml)進行析晶,過濾烘乾得到50.34g米白色固體化合物17,收率78.3%。質譜:516.4(M+H)。
化合物18的合成:向一個1L單口瓶,依次將化合物17(32.5g,62.9mmol,1.0eq)、聯硼酸頻那醇酯(19.18g,75.52mmol,1.2eq),Pd (dppf) Cl2
(0.92g,1.26mmol,0.02eq)、醋酸鉀(12.35g,125.8mmol,2eq),二氧六環(350ml)投入到燒瓶中,油浴加熱到100度左右,保溫攪拌6h,取樣點板17原料反應完。反應液降溫至40℃,反應液減壓濃縮至200ml,加入甲醇(400ml)室溫下攪拌2h,過濾,得到固體加入正己烷(400ml)在50℃時打漿2h,過濾烘乾得到30.35g米白色固體化合物18,收率86.1%。質譜:563.5(M+H)。
化合物B86的合成:向一個1L三口瓶,依次將化合物18(28.0g49.69mmol,1.0eq)、化合物19(23.67g,49.69mmol,1.0eq),K2
CO3
(13.73g,99.38mmol,2.0eq)、Pd132
(0.35g,0.49mmol,0.01eq),甲苯(280ml),乙醇(56ml)去離子水(56ml)投入到燒瓶中,真空、氮氣置換3次,油浴加熱到75度左右,保溫攪拌回流16h,取樣點板18原料反應完。反應液降溫至60度,加入甲苯(200ml),去離子水(100ml),攪拌1h,分液,分液後有機相用矽膠過濾,少量甲苯沖洗矽膠,濃縮有機相得到固體,採用甲苯/甲醇(220ml/250ml)進行重結晶3次,烘乾得到29.47g淡黃色固體,收率71.2%。得到的合成品經過昇華純化得到22.3克淡黃色固體化合物B86,收率75.6%。質譜:833.1(M+H)。1
HNMR(400MHz,CDCl3
)δ8.48(d,1H),7.75(dd,4H),7.62–7.42(m,19H), 7.39(m, J=20.0Hz,9H),7.33–7.14(m,7H),7.08(d,2H),7.00(d,1H),6.86(d,1H)。
化合物B111的合成:選取對應的材料,參照化合物B86的合成方式和處理方法,只需要將對應的原物料變更即可。質譜:897.1(M+H)。1
HNMR(400MHz,CDCl3
)δ8.48(d,1H),7.96(m,6H),7.75(m,4H),7.60–7.34(m, 16H), 7.33-7.15(m,13H),7.08(d,2H),7.00(d,1H),6.86(d,1H)。
化合物B130的合成:選取對應的材料,參照化合物B86的合成方式和處理方法,只需要將對應的原物料變更即可。質譜:913.2(M+H)。1
HNMR(400MHz,CDCl3
)δ8.48(d,1H),7.95–7.79(m,6H),7.60–7.44(m,14H), 7.36(m,J=13.6Hz,7H), 7.30–7.15(m,8H), 7.08(d,2H), 7.00(d,1H), 6.86(d,1H), 1.69(s,12H)
化合物B137的合成:選取對應的材料,參照化合物B86的合成方式和處理方法,只需要將對應的原物料變更即可。質譜:679.8(M+H)。1
HNMR(400MHz,CDCl3
)8.48(d,1H),8.13–7.94(m,3H),7.84(d,2H),7.63–7.46(m, 9H),7.45–7.29(m,5H),7.29–7.13(m,9H),7.04(d,J=40.0Hz,3H),6.86(d,1H)。
應用例:
(1)化合物性能對比:本發明的化合物在OLED器件中可作為光提取層材料,具有較高的玻璃化轉變溫度、較高的折射率、可見光區較小的折射率差值。基本性能列於下表1
表1:折射率對比:
玻璃化溫度(℃) | 昇華溫度(℃) | 折射率 | 折射率差值 | |||||
@450nm | @520nm | @630nm | ΔB-G | ΔB-R | ΔG-R | |||
化合物A1 | 150 | 370 | 2.09 | 2.03 | 1.97 | 0.03 | 0.12 | 0.06 |
化合物A16 | 152 | 378 | 2.04 | 1.99 | 1.95 | 0.06 | 0.09 | 0.04 |
化合物A17 | 141 | 365 | 2.11 | 2.06 | 1.99 | 0.05 | 0.12 | 0.07 |
化合物A22 | 134 | 365 | 2.10 | 2.01 | 1.97 | 0.09 | 0.13 | 0.06 |
化合物B86 | 149 | 370 | 2.15 | 2.07 | 2.03 | 0.08 | 0.12 | 0.04 |
化合物B111 | 154 | 380 | 2.05 | 1.98 | 1.95 | 0.07 | 0.10 | 0.04 |
化合物B130 | 152 | 378 | 2.15 | 2.09 | 2.04 | 0.06 | 0.11 | 0.05 |
化合物B137 | 124 | 363 | 2.07 | 1.99 | 1.96 | 0.08 | 0.11 | 0.03 |
HTM1 | 134 | 385 | 1.99 | 1.91 | 1.85 | 0.08 | 0.14 | 0.06 |
(2)有機電致發光器件的製作
將50mm*50mm*1.0mm的具有ITO(100nm)透明電極的玻璃基板在乙醇中超聲清洗10分鐘,再150度烘乾後經過N2 Plasma處理30分鐘。將洗滌後的玻璃基板安裝在真空蒸鍍裝置的基板支架上,首先在有透明電極線一側的面上按照覆蓋透明電極的方式蒸鍍化合物HATCN,形成膜厚為5nm的薄膜,緊接著蒸鍍一層HTM1形成膜厚為60nm的薄膜,再在HTM1薄膜上蒸鍍一層HTM2形成膜厚為10nm的薄膜,然後,在HTM2膜層上再採用共蒸鍍的模式蒸鍍主體材料CBP和摻雜材料,膜厚為30nm,主體材料和摻雜材料比例為90%:10%。在發光層上再依次按照下表的搭配蒸鍍BCP(5nm)作為空穴阻隔層材料、Alq3
(30nm)作為電子傳輸材料,接著在電子傳輸材料層之上蒸鍍LiF(1nm) 作為電子注入材料,接著再採用共蒸鍍的模式蒸鍍Mg/Ag(18nm,1:9)作為陰極材料,最後在陰極材料之上按照下表的搭配蒸鍍CPL(50nm)作為光提取層材料。
器件性能評價
將上述器件進行器件性能測試,在各實施例和比較例中,使用恒定電流電源(Keithley2400),使用固定的電流密度流過發光元件,使用分光輻射倆都系(CS2000)測試發光波譜,同時測定器件的發光效率。結果如下表2:
表2:
器件 | CPL | 電流效率Cd/A @3000nits |
實施例1 | 化合物A1 | 52 |
實施例2 | 化合物A16 | 52 |
實施例3 | 化合物A17 | 53 |
實施例4 | 化合物A22 | 51 |
實施例5 | 化合物B86 | 50 |
實施例6 | 化合物B111 | 49 |
實施例7 | 化合物B130 | 52 |
實施例8 | 化合物B137 | 51 |
對比例1 | HTM1 | 48 |
對比上述表2中的資料可知,使用本發明的化合物應用於有機電致發光器件的光提取層材料,相較於對比化合物發光效率表現出更加優越的性能。
如上所示,含有本發明結構的咪唑並吡啶的芳胺類化合物具有昇華溫度低,熱穩定性好,折射率高、可見光區折射率差異小等優點,能夠大幅改善光的取出效率、薄膜狀態的穩定性。通過使用該系列化合物製備的OLED器件,能夠得到較高的效率,並且改善其耐用性。綜上所述,該類化合物作為光提取層材料,具有應用於AMOLED產業的可能。
Claims (10)
- 一種咪唑並吡啶的芳胺類化合物,其結構式如式(I)所示:
- 如請求項1所述的化合物,其結構式如式(II)所示:
- 如請求項2所述的化合物,其中,R1為C1-C8烷基取代或未取代的C6-C20的亞芳基、C1-C8烷基取代或未取代的C2-C18的亞雜芳基;其中R2為C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的雜芳基;其中Ar1為取代或未取代的C6-C20的芳基;Ar2為取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環、取代或未取代的C6-C20的芳胺基;其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換;所述取代為被氘、C1-C8烷基、苯基、萘基或聯苯基取代。
- 如請求項3所述的化合物,其中,R1為C1-C4烷基取代或未取代的C6-C10的亞芳基、C1-C4烷基取代或未取代的C2-C8的亞雜芳基;其中Ar1為C1-C4烷基取代或未取代的C6-C10的芳基;R2為C1-C4烷基取代或未取代的C6-C10的芳基、C1-C4烷基取代或未取代的C6-C8的雜芳基;其中Ar2為取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環、取代或未取代的C6-C20的芳胺基;其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換;所述取代為被氘、C1-C4烷基、苯基、萘基或聯苯基取代。
- 如請求項1所述的化合物,其結構式如式(IV)所示:
- 如請求項6所述的化合物,其中,R1為C1-C8烷基取代或未取代的C6-C20的亞芳基、C1-C8烷基取代或未取代的C2-C18的亞雜芳基;其中R2為C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的雜芳基;其中Ar1為取代或未取代的C6-C20的芳基,A為取代或未取代的C6-C20的亞芳基、取代或未取代的C6-C20的亞雜芳基;其中雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換;所述取代為被氘、C1-C8烷基、苯基、萘基或聯苯基取代。
- 如請求項1至7中任一項所述的化合物,其中,X1、X2、X3、X4獨立的表示為CR0,R0獨立的選自氫、C1-C8烷基。
- 一種如請求項1至9中任一項所述的化合物在OLED器件中的應用,所述的應用為請求項1至9中任一項所述的化合物作為OLED器件的光提取層材料。
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EP2067778A1 (en) * | 2007-12-03 | 2009-06-10 | Semiconductor Energy Laboratory Co., Ltd. | Quinoxaline derivative, and light emitting element, licht emitting device and electronic appliance using the same |
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