TW201004904A - Novel materials for organic electroluminescent devices - Google Patents
Novel materials for organic electroluminescent devices Download PDFInfo
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- TW201004904A TW201004904A TW098111009A TW98111009A TW201004904A TW 201004904 A TW201004904 A TW 201004904A TW 098111009 A TW098111009 A TW 098111009A TW 98111009 A TW98111009 A TW 98111009A TW 201004904 A TW201004904 A TW 201004904A
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- 239000000463 material Substances 0.000 title claims abstract description 53
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
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- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical group O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
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- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/573—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with three six-membered rings
- C07C13/58—Completely or partially hydrogenated anthracenes
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/58—Naphthylamines; N-substituted derivatives thereof
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
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- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
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- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
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- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
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- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/30—Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
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- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
201004904 六、發明說明: 【發明所屬之技術領域】 本發明關於有機半導體及其在有機電子裝置中的用途 【先前技術】 以有機半導體發展出許多不同類型之電子應用。以這 ❿ 些有機半導體用作功能性材料的有機電發光裝置(OLED )之結構係敘述於例如US 4539507、US 5151629、 EP 067646 1及WO 98/27 1 3 6中。然而,仍希望進一步改 進這些裝置於高品質及長效顯示器的使用。因此,目前有 特別改進發藍光之有機電發光裝置之壽命及效率的需求。 此外,有必要使化合物具有高的熱安定性及高的玻璃轉換 溫度,且可使其昇華而不分解。高的玻璃轉換溫度爲特別 在高溫下使用所必需的,以求達成長的壽命。 # 對改進用於發螢光體及發磷光體之材料,例如主體材 料有持續的要求,但是亦希望特別在電荷傳輸材料(亦即 電洞-及電子-傳輸材料)及電荷阻擋材料的情況中有進一 步改進。特別地這些材料的性質時常限制有機電發光裝置 的壽命及效率。 出乎意外地發現在兩個苯基各自的3’-及5’·位置上被 取代之9,9-二苯基苐衍生物非常高度適合於有機電發光裝 置中使用’其得到超越先前技藝的改進。這同樣適用於假 設使用代替蒹的9,1〇-二氫蒽衍生物或對應之雜環衍生物 -5- 201004904 。本發明因此關於這些化合物及其在有機電子裝置中的用 途。取決於苯基上的取代作用,根據本發明的化合物特別 適合作爲電洞傳輸材料、電子-或激子·阻擋材料、發螢光 或發憐光化合物之基質材料、電洞阻擋材料及電子傳輸材 料。與依照先前技藝之材料相比,根據本發明的材料能使 相同或改進壽命之有機電子裝置的效率增加。此外,這些 化合物具有高的熱安定性。通常這些材料非常高度適合於 有機電子裝置中使用,因爲彼等具有高的玻璃轉換溫度。 對應延伸之結構,特別爲茚並弗結構及茚並咔唑結構同樣 具有非常好的性質。 可以 US 5,698,740、JP 2005/085599 及 JP 2007/04 905 5述及爲最新的先前技藝。US 5,698,74 0及 JP 2005/085588揭示9,9-二苯基莽衍生物,在兩個苯基各 自上被至少一個胺基或經單-或二取代之胺基取代。僅明 確地揭示在苯基各自的4’·位置上,亦即與弗鍵聯的對位 上被胺基取代之結構。未揭示在一個苯基上被複數個胺基 取代之結構。JP 2007/04905 5揭示9,9-二苯基莽衍生物, 在兩個苯基中至少一個上被至少一個經取代或未經取代之 吡咯或苯並咪唑基團取代。僅明確地揭示在苯基各自的 4-位置上,亦即與莽鍵聯的對位上被胺基取代之結構。未 揭示在一個苯基上被複數個吡咯或苯並咪唑基團取代之結 構。然而,在這些申請案中所揭示之取代樣式未得到在有 機電子裝置中使用時具有足夠好的性質之化合物。出乎意 外地發現尤其在兩個苯基各自的3及5’-位置上的同步取 -6- 201004904 代爲根據本發明的化合物有好的性質之原因。 此外,\^0〇5/〇53〇55揭示在每個三阱基團的3,5-位 置上攜帶苯基的9,9-雙(三畊基)莽作爲發磷光的電發光 裝置中的電洞阻擋材料。然而,化合物的效應係歸因於分 子中存在的三畊基團。在三畊的3,5_位置上存在的取代基 未被授予任何重要性。 φ 【發明內容】 爲清楚起見’ 9,9-二苯基蕗之結構及編號顯示於下:
本發明因此關於式(1)化合物
式⑴ 其中下述適用於所使用之符號: 201004904 X 在各出現場合係相同或不同地爲CR1或N,其中在各 環中最多3個基團X代表N; 或兩個直接鄰接之基團X代表下列式(7)之單元
其中虛線鍵表示單元與鄰接之C或N原子之鍵聯; 〇 Y 在各出現場合係相同或不同地爲單鍵或選自BR1、 ¢(1^)2、C( = 0)、C( = NR1) > C( = C(R1)2) ' Si(Kl)2 ' NR1、PR1、P( = 〇)R1、O、S、S( = 0)、S( = 0)2、 、CUWh-NR1 或 CRkCR1 之基團; Z 在各出現場合係相同或不同地爲CR1或N,其中在各 環中最多2個符號Z代表N; R 在各出現場合係相同或不同地爲Cl、Br、I、三氟甲 磺酸酯、B(OR2)2、B(R2)2、B(N(r2)2)2、NAr2、 ❿ N(R2)2、SiAr3、Si(R2)3、C( = 0)Ar、C( = 0)R2、OAr、 OR2、SAr、SR2 ' s( = 0)Ar、S( = 〇)R2、S( = 〇)2Ar、 S( = 0)2R2、PAr2、P(R2)2、p( = 〇)Ar2、P( = 〇)(R2)2 或 具有5至60個芳族環原子之芳族或雜芳族環系統, 其可被一或多個基團R1取代;
Ar 在各出現場合係相同或不同地爲具有5至3〇個芳族 環原子之芳族或雜芳族環系統,其可被一或多個 族基團R1取代;在此與相同的氮或磷原子鍵結的兩 -8 - 201004904 個基團Ar亦可以單鍵或選自B(R2)、C(R2)2、Si(R2)2 * 、C = 0、C = NR2、C = C(R2)2、O、S、S = 0、S02、 N(R2)、P(R2)及P( = 〇)R2之橋互相連接; R1 在各出現場合係相同或不同地爲H、D、F、Cl、Br、 I、CHO、N(R2)2、N(Ar)2、C( = 0)Ar、P( = 0)(Ar)2、 S( = 0)Ar、S( = 0)2Ar、CR2 = CR2Ar、CN、N02、 si(R2)3、b(or2)2、b(r2)2、B(N(R2)2)2、0S02R2 ;具 0 有1至40個C原子之直鏈烷基、烯基、炔基、烷氧 基或硫烷氧基或具有3至40個C原子之支鏈或環狀 烷基、烯基、炔基、烷氧基或硫烷氧基,其中每個可 被一或多個基團R2取代,其中一或多個未鄰接之 CH2 基團可被 R2C = CR2、C 三 C、Si(R2)2、Ge(R2)2、 Sn(R2)2、C = 0、C = S、C = Se、C = NR2、P( = 〇)(R2)、 SO、S02、NR2、0、s或 CONR2替換,且其中一或 多個H原子可被F、Cl、Br、I、CN或N〇2替換;或 • 具有5至60個芳族環原子之芳族或雜芳族環系統, 其可在各情況中被一或多個基團R2取代;或具有5 至60個芳族環原子之芳氧基或雜芳氧基,其可被一 或多個基團R2取代;或該等系統之組合;二或多個 鄰接之取代基R1在此亦可互相形成單-或多環脂族或 芳族環系統; R2 在各出現場合係相同或不同地爲H、D或具有1至20 個C原子之脂族、芳族及/或雜芳族烴基,另外,其 中Η原子可被F替換;二或多個鄰接之取代基R2在 -9- 201004904 此亦可互相形成單-或多環脂族或芳族環系統; η 爲1或2, 下列的化合物係從本發明排除:
式(1)化合物具有較佳爲大於7〇°C,特別佳爲大於 100°C,最特別佳爲大於ll〇°C之玻璃轉換溫度Το。 如式(1 )所明白,n = 2意謂在3,5-位置上經取代的 兩個芳基係鍵結在化合物中的菲或對應之衍生物的9,9-位 置上,而n=l意謂有一個此芳基及另外一個基團R1存在 〇 就本發明的目的而言,芳基含有6至60個C原子; 就本發明的目的而言’雜芳基含有2至60個C原子及至 少一個雜原子,其先決條件係C原子與雜原子之總數是至 少5個。雜原子較佳地選自N、0及/或S。芳基或雜芳 基在此意謂單一芳族環’亦即苯,或單一雜芳族環,例如 吡啶、嘧啶、噻吩等’或縮合之芳基或雜芳基,例如萘、 蒽、芘、喹啉、異喹啉等。
就本發明的目的而言’芳族環系統含有6至60個C -10- 201004904 原子於環系統中。就本發明的目的而言,雜芳族環系統含 有2至60個C原子及至少一個雜原子於環系統中,其先 決條件係C原子與雜原子之總數是至少5個。雜原子較佳 地選自N、0及/或S。就本發明的目的而言,意欲以芳 族或雜芳族環系統意謂不一定只含有芳基或雜芳基,反而 其中複數個芳基或雜芳基亦可被短鏈非芳族單元(較佳爲 少於1 〇%非Η之原子),諸如sp3-混成之C、N或〇原 φ 子中斷之系統。因此,例如亦意欲以諸如9,9’-螺二弗、 9,9-二芳基葬、三芳基胺、二芳基醚、二苯乙烯、二苯基 酮等之系統意謂就本發明目的的芳族環系統。芳族或雜芳 族環系統同樣意謂其中複數個芳基或雜芳基以單鍵互相連 結之系統,例如聯苯、三聯苯或聯吡啶。 就本發明的目的而言,(^-至C4G-烷基(其中個別的 Η原子或CH2基團可另外被上述基團取代)特別佳地意謂 甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁 • 基、第三丁基、2-甲基丁基、正戊基、第二戊基、環戊基 、正己基、環己基、正庚基、環庚基、正辛基、環辛基、 2 -乙基己基、三氣甲基、五氣乙基及2,2,2-三氣乙基。就 本發明的目的而言’烯基特別意謂乙烯基、丙烯基、丁烯 基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環 庚烯基、辛烯基或環辛烯基。就本發明的目的而言,炔基 特別意謂乙快基、丙炔基、丁炔基、戊炔基、己炔基、庚 炔基或辛炔基。C! _至C4〇-院氧基特別佳地意謂甲氧基、 三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、 -11 - 201004904 異丁氧基、第二丁氧基、第三丁氧基或2-甲基丁氧基。 具有5-60個芳族環原子之芳族或雜芳族環系統(其亦可 在各情況中被上述基團R取代且可經由任何所欲位置與芳 族或雜芳族環系統連結)特別意謂從苯、萘、蒽、菲、苯 並蒽、芘、筷、茈、螢蒽、並四苯、稠五苯、苯並芘、聯 苯、亞聯苯、三聯苯、亞三聯苯、莽、螺二葬、二氫菲、 二氫芘、四氫芘、順-或反-茚並荛、參茚並苯、異參茚並 苯、螺參茚並苯、螺異參茚並苯、呋喃、苯並呋喃、異苯 並呋喃、二苯並呋喃、噻吩、苯並噻吩、異苯並噻吩、二 苯並噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異 喹啉、吖啶、菲啶、苯並-5,6-喹啉、苯並-6,7-喹啉、苯 並-7,8-喹啉、吩噻畊、吩噁畊、吡唑、吲唑、咪唑、苯並 咪哩、萘咪唑、菲咪唑、吡啶咪唑、妣畊咪唑、喹噁啉咪 哩、嚼挫、苯並嚷哩、萘嚼哩、惠嚼哩、菲喔哩、異螺哩 、1,2 -噻唑、噻唑、苯並噻唑、嗒π并、苯並嗒π并、嘧 啶、苯並嘧啶、喹噁啉、1,5-二氮雜蒽、2,7-二氮雜芘、 2,3 -二氮雜在、丨,6 ·二氮雜违、1,8 -二氮雜苑、4,5 -二氮雜 芘、4,5,9,10 -四氮雜茈、吡拼、吩畊、吩噁畊、吩噻畊、 螢紅環、萘陡 '氮雜咔嗤、苯並咔咐、啡啉、丨,2,3 -三哩 、1,2,4-三唑、苯並三唑、丨,2,3·噁二唑、丨,2,4-噁二唑、 1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二 唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5 -三 Π并、1,2,4 -三 _、1,2,3-三 Oft、四唑、I,2,4,5-四畊、12,3,4-四拼、 1,2,3,5-四畊、嘌呤、蝶啶、吲哚畊及苯並噻二唑所衍生 201004904 之基團。 * 在本發明較佳的具體例中,符號X在各出現場合係 相同或不同地代表CR1或N,其中在弗單元中每一環最多 的一種符號X代表N且在莽單元的9-位置上的取代基中 的所有符號X皆代表CR1或所有符號X皆代表N。在本 發明更佳的具體例中,兩個鄰接之基團X確切地代表上 述式(7)之單元。在弗的9-位置上的取代基因此較佳地 φ 代表經3,5 -取代之苯基或三畊。對應之情況適用於假設中 心單元不代表蕗,反而代表以式(1 )涵蓋的其他衍生物 中之—。符號X特別佳地代表c R1。 在式(7)單元中的符號Z較佳地代表CR1。 式(1)化合物較佳的具體例爲式(2) 、(3) 、(8 )、(9 ) 、( 1 〇 )及(1 1 )化合物:
13- 201004904
其中所使用之符號及下標具有以上指示之意義° 在本發明較佳的具體例中,在式(1) 、(2) ' (3 )、(8) 、(9) 、(10)或(11)化合物的6_員環中 的符號Y代表單鍵或選自C^R1);:、〇或NR1之基團’特 別佳地代表單鍵,且在5 -員環中的符號 Y較佳地代表選 自(:(1^)2、Ο或NR1之基團,特S!J佳地代表¢:(1^)2或N ,最特別佳地代表C ( R1 ) 2。 因此,優先選擇爲式(2a) 、(3a) 、(8a) 、(8b )、(9a) 、(9b) 、(10a) 、(10b) 、(ua)及( 1 1 b )化合物: 201004904
-15- 201004904
其中所使用之符號及下標具有以上述及之意義。 在本發明較佳的具體例中,n = 2。 式(1 )化合物更佳的具體例爲式(4a )及(4b )化 β
式(4a)
式(4b) 201004904 其中所使用之符號具有以上指示之意義。 本發明特別佳的具體例爲下列式(4c) 、(4d)、( 8c) 、 ( 8d) 、 (9c) 、 ( 9d ) 、 (10c) 、 (lOd)、( 1 1 c )及(1 1 d )化合物:
-17- 201004904
其中所使用之符號及下標具有以上述及之意冑。 在本發明進一步的較佳具體例中,在上述式之化合物 中的符號R在各出現場合係相同或不同地代表NAr2、 C( = 〇)Ar、P( = 0)Ar2或具有5至30個芳族環原子之芳族 或雜芳族環系統’其可被一或多個非芳族基團r1取代。 假設R與苯基鍵結’則R特別佳地在各出現場合係相同 或不同地代表(較佳爲相同地代表)ΝΑγ2或C( = 0)Ar, 最特別佳地代表NAr2。假設R與三畊基團鍵結,則r特 別佳地代表具有5至10個芳族環原子之芳基或雜芳基。 更佳的取代基R爲CM、Br、I及三氟甲磺酸酯,特別爲 Br,因爲這些爲合成更多根據本發明的化合物之有價値的 201004904 中間物。 在本發明更佳的具體例中,在上述式之化合物中的所 有符號R皆經相同地選擇。可以更容易合成取得化合物來 解釋此優先選擇。 假設基團R或R1代表基團N(Ar) 2,則此基團較佳 地選自式(5)或式(6)之基團··
式(5) 式⑹ 其中R2具有上述指示之意義,且: 9 E 代表單鍵、0、S、N(R2)或 C(R2)2 ;
Ar1在各出現場合係相同或不同地爲具有5至20個芳族 環原子之芳族或雜芳族環系統或具有15至30個芳族 環原子之三芳胺基團,其中每個可被一或多個基團 R2取代,較佳爲具有6至14個芳族環原子之芳基或 雜芳基或具有18至30個芳族環原子,較佳爲具有 18至22個芳族環原子之三芳胺基團,其中每個可被 一或多個基團R2取代; P 在各出現場合係相同或不同地爲〇或1。 -19- 201004904
Ar1特別佳地在各出現場合係相同或不同地代表苯基 、聯苯基、1-萘基、2-萘基、2-、3-或4-三苯胺、1-或2-萘基二苯胺(其中每個可經由萘基或苯基鍵結)或1-或 2·二萘基苯胺(其中每個可經由萘基或苯基鍵結)、N-味 唑基或N-苯基-2-咔唑基或N-苯基-3-咔唑基。這些基團可 各自被一或多個具有1至4個C原子之烷基或被氟取代。 假設基團R或R1代表芳族或雜芳族環系統,則其較 佳地選自具有5至30個芳族環原子,特別具有6至20個 芳族環原子之芳族或雜芳族環系統,最特別佳地選自苯基 、1-萘基、2-萘基、蒽基、苯蒽基、1-或2-萘蒽基 '聯萘 基、苑基、登意基、2-、3-、4-、5-、6 -或7 -苯並恵基、 N-苯並咪唑基、苯基-N-苯並咪唑基、N-苯基苯並咪唑基 及苯基-N-苯基苯並咪唑基。 在本發明更佳的具體例中,在上述式之化合物中的符 號R1在各出現場合係相同或不同地代表H、F、N(Ar)2、 C( = 〇)Ar、P( = 0)(Ar)2、S( = 0)Ar、S( = 0)2Ar、CR2 = CR2Ar :具有1至10個C原子之直鏈烷基或具有3至10個C 原子之支鏈或環狀院基,其中每個可被一或多個基團R2 取代,其中一或多個未鄰接之CH2基團可被R2C=CR2或 〇替換’且其中一或多個Η原子可被F替換;或具有5至 20個芳族環原子之芳族或雜芳族環系統,其可在各情況 中被一或多個基團R2取代;或該等系統之組合;二或多 個鄰接之取代基R1在此亦可互相形成單-或多環脂族或芳 族環系統。在本發明特別佳的具體例中,在上述式之化合 -20- 201004904 物中的符號R1在各出現場合係相同或不同地代表H、F、 " N(Ar)2 ;具有1至6個C原子之直鏈烷基或具有3至6個 C原子之支鏈或環狀烷基,其中每個可被一或多個基團R2 取代,其中一或多個Η原子可被F替換;或具有5至14 個芳族環原子之芳族或雜芳族環系統,其可在各情況中被 一或多個基團R2取代;二或多個鄰接之取代基R1在此亦 可互相形成單-或多環脂族或芳族環系統。R1特別在各出 φ 現場合係相同或不同地代表H、F、甲基、乙基、異丙基 或第三丁基,特別爲Η。在從溶液處理化合物的情況中, 以具有至多10個C原子之直鏈或支鏈烷基亦較佳。 在對應選擇之Υ上的橋Υ中存在的較佳基團R1在各 出現場合係相同或不同的基團,且較佳地選自Η;具有1 至6個C原子之直鏈烷基或具有3至6個C原子之支鏈 烷基,其中一或多個未鄰接之 CH2基團可被-R2C = CR2-、-Ce C-或-Ο-替換,且其中一或多個Η原子可被F • 替換;或具有6至20個C原子之芳基或具有2至20個C 原子之雜芳基,其中每個可被一或多個基團R2取代;或 二或三個該等系統之組合;在此均與Υ鍵結的基團R1中 之二者亦可互相形成環系統且因此形成螺系統。與橋Υ 鍵結的特別佳基團R1在各出現場合係相同或不同的基團 ,且選自甲基、乙基、異丙基、第三丁基,其中一或多個 Η原子可在各情況中被F替換;或具有6至14個C原子 之芳基,其可被一或多個基團R2取代;兩個基團R1在此 亦可互相形成環系統。在從溶液處理化合物的情況中,以 -21 - 201004904 具有至多10個c原子之直鏈或支鏈烷基亦較佳。假設橋 Y爲基團NR1,則基團R1亦特別佳地選自具有5至20個 芳族環原子之芳族或雜芳族環系統。 較佳的式(1)至(4)化合物的實例具有以下描述之 結構(1 )至(276 )。
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σΝΌ 9 (268) σΝΌ (269) (270) σΝΌ j 9 ^ywo (271) (272) σΝΌph ρ lprNt) σΝΌ ό (273) (274) -58- 201004904 參 χ /X ό ψ N丫 N ό (275) (276) 根據本發明的式(1)化合物可以熟習此技藝者在一 般條件下已知的合成步驟製備。用於根據本發明的對稱取 代之化合物的起始化合物可爲例如3,3’,5,5’-四溴二苯基 酮(Eur. J. Org. Chem. 2006, 2523-2529 )。例如依照流 程1,其可藉由與經取代或未經取代之2-鋰聯苯、2-鋰二 苯醚、2-鋰二苯基硫醚、2- (2-鋰苯基)-2-苯基-1,3-二氧 戊環或2-鋰苯基二苯胺反應而轉化成對應之三芳基甲醇 ,其接著在酸性條件下環化,例如在乙酸及無機酸(諸如 溴化氫)的存在下。此反應所必要的有機鋰化合物可以對 應之芳基溴化物(2·溴聯苯、2-溴二苯醚、2-溴二苯基硫 醚、2- ( 2·溴苯基)-2-苯基-1,3-二氧戊環、2-溴苯基二苯 胺等)使用烷基鋰化合物(諸如正丁基鋰)的轉金屬化作 用而製備。當然有可能使用類似對應之格任亞(Grignard )化合物。 -59- 201004904 流程1
以此方式所生產之四溴化物可以熟習此技藝者已知的 方法進一步轉化。與硼酸的以鈀催化之反應(鈴木( 參
Suzuki)偶合)或與有機鋅化合物的以鈀催化之反應(根 岸(Negishi)偶合)得到根據本發明的芳族或雜芳族化 合物(流程2)。 流程2
X= B(OH)2,ZnBr. MgBr,等. 與胺的以鈀催化之反應(哈特維-布希沃德(Hartwig_ Buchwald )偶合)得到根據本發明的芳族或雜芳族胺(流 程3)。 -60- 201004904 流程3
溴官能性可藉由使用有機鋰化合物或格任亞化合物的 Φ 轉金屬化作用而轉化成親電子性基團,其接著與多種親電 子劑(諸如鹵化芳基硼、醛、酮、腈、酯、鹵素酯、二氧 化碳、鹵化芳基膦、鹵基亞硫酸、鹵芳基磺酸等)偶合, 其中以該方式所獲得的化合物可爲根據本發明的最終產物 或者爲可進一步反應的中間物。這係以參考用於製備根據 本發明的酮、氧化膦及苯並咪唑之實例的實例方式例證( 流程4)。 ❷ -61 - 201004904 流程4
1)Ar2PCI 2)H202
1)C02
/ PPh3 / 0(S02CF3)
根據本發明的不對稱取代之化合物可根據流程5的順 序而獲得,此流程係從莽酮及類似的芳基酮開始,藉由將 -62- 201004904 芳基-金屬化合物(例如,1 -鋰基-3,5 -二溴苯)加到羰官 能基上,將溴化芳族化合物以建立一種官能度的上述方法 中之一轉化,並接著將其他的官能度經由以酸催化之夫里 得-夸夫特(Friedel-Crafts)芳基化作用引到l,3-二溴苯 上及將溴化芳族化合物以上述方法中之一轉化(參見例如 Org. Lett. 200 1 , 3 ( 1 5 ) , 228 5 ) 〇
-63- 201004904 可對應地合成式(1)的對應之茚並弗衍生物、茚並 - 昨唑衍生物及其他衍生物。 _ 本發明另外關於一種用於製備式(1)化合物之方法 ’其包含將雙(3,5-二溴)二苯基酮與經取代或未經取代 之2·鋰聯苯、2-鋰二苯醚、2-鋰二苯基硫醚、2-(2-鋰苯 基)-2·苯基-1,3·二氧戊環、2-鋰苯基二苯胺或對應之格 任亞化合物反應,得到三芳基甲醇,接著在酸性條件下環 化及隨意地接著與溴基團進一步反應。 參 上述根據本發明的化合物,特別爲被反應性脫離基, 諸如溴、碘、三氟甲磺酸酯、甲苯磺酸酯、硼酸或硼酸酯 取代之化合物可用作生產對應之二聚物、三聚物、四聚物 、五聚物、寡聚物、聚合物之單體或用作樹枝狀聚合物之 核心。寡聚合作用或聚合作用在此較佳地係經由鹵素官能 度或硼酸官能度來進行。這特別適用於其中基團R1各代 表反應性脫離基,特別爲選自上述之基團的式(4)化合 物。 ⑩ 本發明因此另外關於含有一或多種式(Π化合物的 二聚物、三聚物、四聚物、五聚物、寡聚物、聚合物或樹 枝狀聚合物,其中一或多個基團Rl或R2代表在二聚物、 三聚物、四聚物或五聚物中的式(1)化合物之間的鍵或 從式(1)化合物到聚合物、寡聚物或樹枝狀聚合物的鍵 ,或其中此鍵結係經由在基團R上的取代基發生。就本發 明的目的而言’寡聚物意謂具有至少6個式(1)單元之 化合物。聚合物、寡聚物或樹枝狀聚合物可經共軛、部分 -64- 201004904 共軛或未經共軛。三聚物、四聚物、五聚物、寡聚物或聚 合物可爲直鏈或支鏈。在以直線連結的結構中,式(1) 單元可直接互相連結或經由二價基團互相連結,例如經由 經取代或未經取代之伸烷基、經由雜原子或經由二價芳族 或雜芳族基團。在支鏈結構中,例如三或多個式(1)單 元可經由三價或多價基團連結,例如經由三價或多價芳族 或雜芳族基團,得到支鏈三聚物、四聚物、五聚物、寡聚 0 物或聚合物。 與上述相同的優先選擇適用於二聚物、三聚物、四聚 物、五聚物、寡聚物及聚合物中的重複之式(1)單元。 在此較佳的重複單元因此亦爲上述式之單元。 將根據本發明的單體與更多單體均聚合或共聚合,以 製備寡聚物或聚合物。適合且較佳的共單體係選自弗(例 如,依照EP 842208或WO 00/22026)、螺二莽(例如, 依照 EP 707020、EP 894 1 07 或 WO 06/06 1 1 8 1 )、對-苯 Φ 撐(例如’依照WO 92/1 8552 )、咔唑(例如,依照 WO 04/070772 或 WO 04/1 1 3468 )、噻吩(例如,依照 EP 1028136)、二氫菲(例如,依照 WO 05/014689)、 順-及反-茚並莽(例如,依照WO 04/041901或 WO 04/1 13412 )、酮(例如,依照 w〇 05/0403 02 )、菲 (例如’依照WO 05/104264或WO 07/017066)或亦選自 複數個這些單元。聚合物 '寡聚物及樹枝狀聚合物亦經常 含有更多單元,例如發光(發螢光或發磷光)單元,諸如 乙烯基三芳胺(例如’依照WO 07/068325)或發磷光金 -65- 201004904 屬錯合物(例如,根據wo 06/003000 ),及/或電荷傳 輸單兀。假設一或多個基團R代表NAr2,則根據本發明 的重複單元在此特別適合作爲電洞之電荷傳輸單元。 本發明另外關於包含至少一種式(1)化合物或對應 之二聚物、三聚物、四聚物、五聚物、寡聚物、聚合物或 樹枝狀聚合物與至少一種另一化合物之混合物。假設式( 1 )化合物係用作基質材料,則另一化合物可爲例如發螢 光或發磷光摻雜劑。適合的發螢光或發磷光摻雜劑係關於 有機電發光裝置而述及於下且亦較佳於根據本發明的混合 物。假設式(1)化合物爲電洞傳輸或電子傳輸化合物, 則另一化合物亦可爲摻雜劑。適合的摻雜劑係關於有機電 發光裝置而述及於下。 本發明再另外關於包含至少一種式(1)化合物或對 應之二聚物、三聚物、四聚物、五聚物、寡聚物或聚合物 及至少一種有機溶劑之溶液。此類型之溶液爲從溶液生產 有機電子裝置所必要的,例如以旋轉塗佈或以印刷法。 根據本發明的式(1)化合物及對應之二聚物、三聚 物、四聚物、五聚物、寡聚物、聚合物或樹枝狀聚合物適 合用於電子裝置中,特別於有機電發光裝置(OLED, PLED)中。化合物係視其取代用於各種功能及層中。較 佳的具體例在此符合上述之式。 本發明因此另外關於式(1)化合物或對應之二聚物 、三聚物、四聚物、五聚物、寡聚物、聚合物或樹枝狀聚 合物於電子裝置中的用途’特別於有機電發光裝置中。 -66- 201004904 本發明再另外關於包含至少一種式(1)化合物或對 • 應之二聚物、三聚物、四聚物、五聚物、寡聚物、聚合物 或樹枝狀聚合物之有機電子裝置,特別爲包含陽極、陰極 及至少一個發光層之有機電發光裝置’其特徵在於至少一 層可爲發光層或另一層的有機層包含至少一種式(1)化 合物或對應之二聚物、三聚物、四聚物、五聚物、寡聚物 、聚合物或樹枝狀聚合物。 Φ 除了陰極、陽極及發光層以外,有機電發光裝置亦可 包含更多層。在各情況中,該等層係例如選自一或多個電 洞注射層、電洞傳輸層、電洞阻擋層、電子傳輸層、電子 注射層、電子阻擋層、激子阻擋層、電荷產生層(IDMC 2003,Taiwan ; Session 21 OLED (5),T. Matsumoto,Τ· Nakada,J. Endo, K. Mo ri,N · Kawamura,A. Y〇ko i 5 J _ Kido 之 Multiphoton Organic EL Dei vce Having Charge Generation Layer)及/或有機或無機p/n接合。此外, φ 層(特別爲電荷傳輸層)亦可經摻雜。層之摻雜可有利於 改進之電荷傳輸。然而,在此應指出該等層沒必要每個層 都存在,且層的選擇總是取決於所使用之化合物且亦特別 取決於裝置是否爲發螢光或發磷光之電發光裝置。 在本發明更佳的具體例中,有機電發光裝置包含複數 個發光層,其中至少一個有機層包含至少一種式(1)化 合物。這些發光層特別佳地總計具有複數個介於380奈米 與750奈米之間的最大發光値,整體上造成發白光,亦即 能夠發螢光或發磷光且發藍光及黃光、橘光或紅光的各種 -67- 201004904 發光化合物被用於發光層中。特別優先選擇爲三層系統, 亦即具有三個發光層之系統,其中這些層中至少一者包含 至少一種式(1)化合物且其中三層顯出發藍光、綠光及 橘光或紅光(基礎結構,參見例如WO 05/011013)。具 有寬帶發光帶且因此顯出發白光的發光體同樣適合於發白 光。 在本發明較佳的具體例中,式(1 )化合物係用作發 光層中的發螢光或發磷光化合物之基質材料。在發磷光化 合物之基質材料的情況中,一或多個基團R及/或R1較佳 地代表 C( = 0)Ar、N(Ar)2、S( = 0)Ar、 S( = 0)2Ar 或 P( = 0)Ar2。相同的優先選擇適用於式(2) 、 (3)及(4 )之結構中的基團R及R1。在發螢光化合物之基質材料 的情況中,一或多個基團R及/或R1較佳地代表芳族或雜 芳族環系統,特別爲含有蒽之芳族環系統。相同的優先選 擇適用於上述式之結構中的基團R及R1。 在包含基質及摻雜劑的系統中,基質材料意謂以較高 比例存在於系統中的組份。在包含一種基質及複數種摻雜 劑的系統中,基質意謂在混合物中的比例最高的組份。 在本發明較佳的具體例中,所使用之基質爲混合物, 其中此混合物的至少一種組份爲式(1)化合物。較佳的 是此混合物的一種組份爲電洞傳輸化合物及其他組份爲電 子傳輸化合物。較佳的電洞傳輸化合物爲芳族胺及咔唑衍 生物。較佳的電子傳輸化合物爲芳族酮。 假設式(1)化合物係用作發光層中的發光化合物之 -68- 201004904 基質材料’則其可與一或多種發磷光材料(三重態發光體 ' )組合使用。就本發明的目的而言,磷光意謂來自具有相 對高的自旋多重性(亦即自旋態> 1 )之激發態,特別爲 來自激發之三重態的發光。就本發明的目的而言,將所有 (特別爲發光)的銥、鈾、餓、金及銅化合物稱爲發磷光 材料。包含式(1)化合物及發光化合物的混合物於是包 含以包含發光體與基質材料的整個混合物爲基準計介於 〇 99與1重量%之間,較佳爲介於98與10重量%之間, 特別佳爲介於97與60重量%之間,特別爲介於95與85 重量%之間的式(1)化合物。混合物對應地包含以包含 發光體與基質材料的整個混合物爲基準計介於1與99重 量%之間,較佳爲介於2與90重量%之間,特別佳爲介 於3與40重量%之間,特別爲介於5與1 5重量%之間的 發光體。 適合的發磷光化合物(=三重態發光體)特別爲在適 • 合的激發時發出較佳爲可見光範圍內的光之化合物,且另 外含有至少一種具有原子序大於20,較佳爲大於38且少 於84,特別佳爲大於56且少於80之原子。所使用之發 磷光體較佳爲含有銅、鉬、鎢、鍊、釕、餓、铑、銥、鈀 、鉑、銀、金或銪之化合物,特別爲含有銥或鉑之化合物 〇 上述發光體的實例揭露於申請案WOO 0/70655、 WO 01/41512、WO 02/0271 4、WO 02/1 5645 > EP 119 1613 、EP 1191612、EP 1191614 及 WO 05/033244 中。上述根 -69- 201004904 據本發明的化合物另外適合作爲發光體。通常所有如根據 先前技藝用於發磷光OLED且爲熟習有機電發光領域之技 藝者已知的發磷光錯合物皆適合,且熟習此技藝者能夠在 沒有本發明的步驟下而使用更多的發磷光錯合物。 假設式(1)化合物係用作發螢光化合物之基質材料 ,則在發光層中的基質材料之比例係介於50.0與99.9重 量%之間,較佳爲介於80.0與99.5重量%之間,特別佳 爲介於90.0與99.0重量%之間。摻雜劑之比例係對應地 介於0.1與50.0重量%之間,較佳爲介於0.1與20.0重 量%之間,特別佳爲介於0.5與1 5重量%之間,最特別 佳爲介於1.0與10.0重量%之間。 較佳的摻雜劑係選自單苯乙烯基胺、二苯乙烯基胺、 三苯乙烯基胺、四苯乙烯基胺、苯乙烯基膦、苯乙烯基醚 及芳基胺之類別。單苯乙烯基胺意謂含有一個經取代或未 經取代之苯乙烯基及至少一個胺(較佳爲芳族胺)之化合 物。二苯乙烯基胺意謂含有兩個經取代或未經取代之苯乙 烯基及至少一個胺(較佳爲芳族胺)之化合物。三苯乙嫌 基胺意謂含有三個經取代或未經取代之苯乙烯基及至少一 個胺(較佳爲芳族胺)之化合物。四苯乙烯基胺意謂含有 四個經取代或未經取代之苯乙烯基及至少一個胺(較佳爲 芳族胺)之化合物。苯乙嫌基特別佳爲二苯乙嫌,其亦可 經進一步取代。對應之膦及醚係以類似於胺予以定義。就 本發明的目的而言,芳基胺或芳族胺意謂含有三個與氮直 接鍵結之經取代或未經取代之芳族或雜芳族環系統之化合 -70- 201004904 物。這些芳族或雜芳族環系統中至少一者較佳爲縮合之環 • 系統,較佳爲具有至少14個芳族環原子。其較佳的實例 爲芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族 筷胺或芳族筷二胺。芳族蒽胺意謂其中一個二芳胺基與蒽 基團直接鍵結之化合物,較佳地在9-位置上。芳族蒽二 胺意謂其中兩個二芳胺基與蒽基團直接鍵結之化合物,較 佳地在9,10-位置上。芳族芘胺、芘二胺、筷胺及筷二胺 Φ 係以類似於上述方式予以定義,其中二芳胺基較佳地在 1-位置或1,6-位置上與芘鍵結。更佳的摻雜劑係選自茚並 弗胺或茚並弗二胺(例如,依照WO 06/122630)、苯並 茚並蕗胺或苯並茚並蕗二胺(例如,依照WO 08/006449 )及二苯並茚並莽胺或二苯並茚並莽二胺(例如,依照 WO 0 7/140847) 。來自苯乙烯基胺之類別的摻雜劑之實 例爲經取代或未經取代之三-二苯乙烯胺或敘述於 WO 06/0003 88、WO 06/058737 ' WO 06/000389 ' 〇 WO 07/0 65549 及 WO 0 7/115610 中的摻雜劑。 在本發明的另一具體例中,式(1)化合物係用作電 洞傳輸材料或電洞注射材料或電子阻擋材料或激子阻擋材 料。化合物於是較佳地被至少一個基團N(Ar)2,較佳地被 至少兩個基團N(A〇2取代,及/或含有更多改進電洞傳 輸的基團。在此特別佳的是所有基團R皆代表Ν(Αγ)2。 基團Ν(Α〇2較佳地係選自上述之式(5)及(6)。這特 別適用於在上述式之結構上的基團R。改進電洞傳輸的更 佳基團爲例如作爲橋Υ基團之NiR1)、S或Ο,或作爲基 201004904 團R或R1之富含電子之雜芳族基團,特別爲噻吩、吡咯 或呋喃。化合物較佳地係用於電洞傳輸或電洞注射或電子 阻擋或激子阻擋層中。就本發明的目的而言,電洞注射層 爲與陽極直接鄰接之層。就本發明的目的而言,電洞傳輸 層爲介於電洞注射層與發光層之間的層。就本發明的目的 而言,電子阻擋或激子阻擋層爲與在陽極面上的發光層直 接鄰接之層。假設式(1)化合物係用作電洞傳輸或電洞 注射材料,則可能較佳的是將其與電子受體化合物摻雜, 例如與F4-TCNQ或與如EP 147688 1或EP 1 596445中所 述之化合物。 在本發明的再另一具體例中,式(1)化合物係用作 電子傳輸層或電洞阻擋層中的電子傳輸材料或電洞阻擋材 料。在此較佳的是基團Y代表c = o、p( = o)、so或so2, 及/或取代基R及/或R1中至少一者代表雜芳基,其代 表缺電子雜環,諸如咪唑、吡唑、噻唑、苯並咪唑、苯並 噻唑、三唑、噁二唑、苯並噻二唑、啡咻等,或代表 C( = 〇)Ar、P( = 0)Ar2、S( = 0)Ar 或 S(0)2Ar。此外,可能較 佳的是將化合物與電子供體化合物摻合。就本發明的目的 而言,電洞阻擋層爲介於發光層與電子傳輸層之間且與發 光層直接鄰接之層。假設式(1)化合物係用作電子傳輸 材料,則可能較佳的是使用其與更多化合物作爲混合物。 較佳的混合物組份爲鹼金靥*化合物,較佳爲鋰化合物,特 別佳爲Liq (唾啉鋰)或Liq衍生物。 重複的式(1)單元可同樣地用作聚合物中的聚合物 -72- 201004904 主鏈、電洞傳輸單元及/或電子傳輸單元。較佳的取代樣 ' 式在此對應於那些上述者。 此外,優先選擇爲有機電發光裝置,其特徵在於·—或 多層係以昇華法的方式塗覆,其中材料係在真空昇華單元 中以低於1(Γ5毫巴,較佳爲低於1CT6毫巴之壓力下蒸汽 沉積。然而,應注意壓力甚至還可更低,例如低於1 〇 -7 毫巴。 • 優先選擇爲有機電發光裝置,其特徵在於一或 多層係以OVPD (有機蒸氣相沉積)法或輔以載體-氣體 昇華法的方式塗覆,其中材料係在介於1〇·5毫巴與1巴 之間的壓力下塗覆。此方法的特殊例子爲OVJP (有機蒸 氣噴射印刷)法,其中材料係經由噴嘴直接塗覆且因此結 構化(例如,M. S. Arnold 等人之 Appl. Phys. Lett. 2008, 92, 053 30 1 )。 此外,優先選擇爲有機電發光裝置,其特徵在於一或 Φ 多層係從溶液生產,諸如以旋轉塗佈或以任何所欲之印刷 法方式,諸如網版印刷、快乾印刷或套版印刷,但是特別 佳爲LITI (以光誘致熱成像,熱轉移印刷)或噴墨印刷 。可溶性化合物爲就此目的所必要的。高溶解度可以適合 的化合物取代作用達成。在此不僅有可能塗覆個別材料之 溶液,且亦有可能塗覆包含複數種化合物,例如基質材料 及摻雜劑之溶液。 在根據本發明的化合物用於有機電發光裝置中時,此 化合物具有下列超越先前技藝之驚人優點: -73- 201004904 ι·根據本發明的化合物具有高的熱安定性且可昇華 而不分解。 2. 在根據本發明的化合物,特別爲那些含有二芳胺 基取代基作爲基團R之化合物用於發磷光之電發 光裝置中的電子/激子阻擋層中時,此化合物得到 與根據先前技藝之材料相比,大爲改進的效率。 3. 根據本發明的化合物,特別爲那些被二芳胺基取 代及/或含有單鍵或S、Ο或N(Ri)作爲基團γ 及/或被富含電子之雜芳族基團取代之化合物非 常高度適合用作電洞注射及電洞傳輸材料且引起 操作電壓減低。 4. 以根據本發明的化合物所生產之OLED通常具有 非常長的壽命。 5_以根據本發明的化合物所生產之OLED通常具有 非常高的量子效率。 本發明的上下文係針對根據本發明的化合物關於 OLED及PLED與對應之顯示器的用途。雖然有此敘述上 的限制,但是熟習此技藝者在沒有進一步的發明步驟下亦 有可能以根據本發明的化合物用於其他的電子裝置中,例 如有機場效電晶體(0-FET)、有機薄膜電晶體(0_TFT )、有機發光電晶體(o-let)、有機積體電路(0-IC ) 、有機太陽能電池(Ο-SC)、有機場淬滅裝置(〇__fqd) 、發光電化學電池(LEC)、有機雷射二極體(〇-雷射) 或有機感光器。 -74- 201004904 本發明同樣關於根據本發明的化合物在對應之裝置中 的用途及這些裝置本身。 本發明係藉由下列實例更詳細敘述,而不想藉此限制 本發明。熟習此技藝者能夠以沒有發明而製備更多根據本 發明的化合物且以其用於有機電子裝置中。 【實施方式】 0 實例: 下列的合成法係在保護性氣體環境下於無水溶劑中進 行,除非有其他另外的指示。溶劑及試劑可購自 ALDRICH或ABCR。前驅物3,3 ’,5,5 ’ -四溴二苯基酮係如 Eur. J. Org. Chem. 2006,25 2 3-2529 中所述而製備。
對應之格任亞化合物係從144·5公克(620毫莫耳) 2-溴聯苯及15.3公克(580毫莫耳)鎂在500毫升四氫呋 喃與250毫升二甲氧基乙烷之混合物中而製備。接著在室 溫下加入在1000毫升四氫呋喃中的224.0公克(450毫莫 -75- 201004904 耳)雙(3,5-二溴苯基)酮之懸浮液,並將混合物再攪拌 12小時。在真空中移除溶劑,將1 000毫升冰醋酸及5毫 升溴化氫加入殘餘物中,並將混合物攪拌1小時。將懸浮 液在回流下加熱半小時後在室溫下攪拌1 2小時。將固體 以抽氣濾出,以300毫升乙醇清洗三次且從甲苯再結晶兩 次。產率:183.2公克(289毫莫耳),64.3%,純度約 99.8% ( HPLC )。
根據本發明的下列化合物係以類似於實例1從對應之 溴化物而獲得(實例2及3 ): 實例 溴 產物 產率 2 \ (T\ /=ν/_ 74.8% Br ΒΓψχ^ΒΓ Br Br 3 oco COO Br Br 58.7%
實例4: 9,9-雙(3, 5-二苯基苯基)莽之合成法 -76- 201004904
φ 將1·〇公克(3.3毫莫耳)三-鄰-甲苯膦及0.5公克( 2.2毫莫耳)乙酸鈀(II)加到在300毫升甲苯、300毫升 1,4 -二噁烷與300毫升水之混合物中的30.4公克(48毫 莫耳)9,9-雙(3,5-二溴苯基)莽、35.4公克(290毫莫 耳)苯基硼酸及121.0公克(570毫莫耳)磷酸三鉀之徹 底攪拌的懸浮液中,並接著將混合物在回流下加熱3小時 。在冷卻之後,將有機相分開,以每次150毫升水清洗三 次且經由矽膠過濾。在真空中移除溶劑且將殘餘物溶解在 Φ 200毫升乙醇中,以抽氣濾出且以100毫升乙醇清洗三次 。將固體從氯苯再結晶三次,且在乾燥之後,在真空中昇 華(ρ=1χ10_5毫巴,T = 320°c)兩次。產率:11.1公克( 18 毫莫耳),37.1 %,純度約 99_9 % ( HPLC )。 根據本發明的下列化合物係以類似於實例4從對應之 硼酸而獲得(實例5-7): -77- 201004904 實例 硼酸 η 產物 產率 5 ΗΟ、β/ΟΗ CtO ΒΓψγΒΓ Βγ Βγ 48.2% 6 η〇、β/〇η ChD ΒΓ^γΒΓ Βγ Βγ 0 6 34.6% 7 '/OH βγΧ7^βγ Βγ Βγ 42.9% 實例8: 9,9-雙(3,5-二苯胺基苯基)莽之合成法
將101毫克(0.50毫莫耳)三-第三丁膦及56毫克( 0.25毫莫耳)乙酸鈀(II)加到在500毫升甲苯中的25.4 -78- 201004904 公克(40毫莫耳)9,9 -雙(3,5 -二溴苯基)弗、 (200毫莫耳)二苯胺及21·1公克(220 [lacuna]之徹底攪拌的懸浮液中’並將混合物在 熱5小時。在冷卻之後’將溶液經由矽膠過濾:S 空中蒸發至乾燥。將殘餘物在乙醇與水的1:1 升混合物中於60°C下攪拌1小時,以抽氣濾迁 毫升乙醇清洗五次且在真空中乾燥。將米黃色E 基甲醯胺再結晶五次及從氯苯再結晶三次,在真 且接著昇華(p = lxHT5毫巴,T = 350 °C )兩次 10.2公克(10毫莫耳),25.0%,純度99.9% ,Tg = 99.8°C。 根據本發明的下列化合物係以類似於實例8 胺及對應之莽而獲得(實例9-13): 33.8公克 毫莫耳) 回流下加 :接著在真 之600毫 ,,以 250 1體從二甲 空中乾燥 。產率: (HPLC ) 從對應之
-79- 201004904 實例 胺 苯 產物 產率 9 HN CtO ΒΓψψΒΓ Br Br Φ qp Φ jaNxx 59.8% 10 HN Br^^TBr Br Br pr OP X>N V X^rNXJ X>NXX X>NXJ 48.3% 11 hP3 b Br^^rBr Br Br op QP QO 53.0% 12 IP Br>^^rBr Br Br 38.1% 13 P HN b ΒΓψψΒΓ Br Br aNX7 iprNiD 〇ΓΝΌ σΝΌ 62.7%
實例14: 9,9-雙(3,5-二咔唑-N-基)莽之合成法 -80- 201004904
Ο 將50·7公克(80毫莫耳)9,9-雙(3,5·二溴苯基)蒹 、78.6公克(470毫莫耳)咔唑及201.7公克(950毫莫 耳)磷酸三鉀在1000毫升對-二甲苯中之懸浮液與500公 克玻璃珠劇烈攪拌。將1.62公克(8.0毫莫耳)三-第三 丁膦及894毫克(4.0毫莫耳)乙酸鈀(II)加到懸浮液 中,接著將其在回流下加熱5天。在冷卻之後,加入 1 000毫升水,並將混合物攪拌12小時且接著過濾。將有 〇 機相分開,以200毫升水清洗三次及接著在真空中蒸發, 得到黏的油。在與3 00毫升乙醇攪拌時形成結晶狀固體, 將其以抽氣濾出且以250毫升乙醇清洗三次。將固體在 3 5 0毫升二甲基甲醯胺中的溶液逐滴加到1 500毫升沸騰 乙醇中。在冷卻之後,將固體以抽氣濾出,從氯苯再結晶 三次,在真空中乾燥且接著在真空中昇華(ρ = ΙχΙΟ-5毫巴 ,T = 370°C )兩次。產率·· 33.2公克(34毫莫耳),42.4 %,純度 99.8% ( HPLC )。 根據本發明的下列化合物係以類似於實例1 4從對應 -81 - 201004904
將67.5毫升正丁基鋰(在己烷中的2.5M溶液)逐滴 -82- 201004904 加到在1000毫升THF中的25.4公克(40毫莫耳)9,9 -雙 * ( 3,5-二溴苯基)苐之冷卻至-78 °C之溶液中,並接著將混 合物在-78 °C下攪拌30分鐘。接著快速加入18·6公克( 180毫莫耳)苯甲腈與50毫升THF之混合物,將混合物 在-78 °C下再攪拌1小時且接著允許溫熱至室溫,加入 100毫升5N氫氯酸且將混合物在回流下沸騰5小時。在 冷卻之後,在真空中於旋轉蒸發器中移除THF,並將殘餘 φ 物溶解在5 00毫升二氯甲烷中,以水及碳酸氫鈉飽和溶液 清洗,直到中性爲止,經硫酸鎂乾燥且經以矽膠之短管柱 濾出。將溶劑在真空中於旋轉蒸發器中蒸發至約50毫升 ,加入300毫升甲醇,並將沉澱固體以抽氣濾出且以100 毫升甲醇清洗一次。在乾燥之後,將米黃色固體從二甲基 甲醯胺再結晶五次,在真空中乾燥且接著昇華(P=lxlO_5 毫巴,T = 360 °C )兩次。產率:14.3公克(19毫莫耳), 48.6%,純度 99.9% ( HPLC )。 ❹ 根據本發明的下列化合物係以類似於實例1 7從對應 之腈而獲得(實例18及19): -83- 201004904
實例20: 9,9·雙((3,5 _雙二苯膦基)苯基)荛之合成法
將67.5毫升正丁基鋰(在己烷中的2.5M溶液)逐滴 加到在1〇〇〇毫升THF中的25.4公克(40毫莫耳)9,9-雙 (3,5-二溴苯基)蕗之冷卻至_78 °C之溶液中,並接著將混 合物在-78 °C下攪拌30分鐘。接著快速加入39.7公克( 180毫莫耳)氯二苯膦與50毫升THF之混合物,將混合 -84- 201004904 ❹
物在-78°C下再攪拌1小時且接著允許溫熱至室溫,在真 空中於旋轉蒸發器中完全移除THF,將殘餘物溶解在500 毫升乙酸乙酯中,逐滴加入150毫升1〇%之過氧化氫並 劇烈攪拌,將混合物再攪拌1 6小時,將水相分開,將溶 劑在真空中於旋轉蒸發器中蒸發至約50毫升,加入300 毫升甲醇,並將沉澱固體以抽氣濾出且以1〇〇毫升甲醇清 洗一次。在乾燥之後,將米黃色固體從氯苯再結晶五次’ 在真空中乾燥且接著昇華(P = lxl〇-5毫巴,T = 390°C )兩 次。產率:12·0公克(11毫莫耳),26.8%,純度99_9 % ( HPLC)。 根據本發明的下列化合物係以類似於實例20從對應 之氯膦而獲得(實例21): 實例 胺 產物 產率 21 27.6% 實例22: 9,9-雙((3,5-雙-Ν-苯基苯並咪唑-2-基)苯基 )莽之合成法 -85- 201004904
a) 9,9-雙(3,5-二氰苯基)荛 將在10 00毫升二甲基乙醯胺中的63.4公克(100毫 莫耳)9,9-雙(3,5-二溴苯基)莽、58.7公克(500毫莫 耳)氰化鋅、3.3公克(50毫莫耳)鋅及11.6公克(10 毫莫耳)肆(三苯膦基)鈀(0)之懸浮液在140°C下攪 拌60小時。在冷卻之後,加入1000毫升濃縮氨溶液,將 混合物再攪拌1小時且以抽氣過濾,並將固體以500毫升 水清洗及以100毫升乙醇清洗三次且在真空中乾燥。產率 :39.8公克(95毫莫耳),95.1%,根據1H-NMR之純度 98%。 b) 9,9-雙(3,5-二羧苯基)莽 將39.8公克(95毫莫耳)9,9-雙(3,5-二氰苯基)莽 在300毫升乙醇與1〇〇毫升水之混合物中的40公克氫氧 化鈉之溶液中於回流下加熱,直到形成澄清溶液爲止(約 1 〇小時)。在冷卻之後,將pH以加入5N氫氯酸調整至 1。將沉澱固體以抽氣濾出,以水清洗,直到流出具有 -86- 201004904 pH = 4-5之母液爲止’抽乾且接著與甲苯共沸乾燥。產率 * : 44.5公克(90毫莫耳),94.8%,根據1H-NMR之純度 98% 〇 c) 9,9-雙((3,5-雙-N-苯基苯並咪唑-2-基)苯基)弗 將44.5公克(90毫莫耳)9,9-雙(3,5-二羧苯基)弗 懸浮在150毫升亞硫醯氯中,並將1滴DMF加到懸浮液 φ 中’接著在60 °C下溫熱,直到氣體完全放出爲止。接著 在真空中移除過量亞硫醯氯,將殘餘物溶解在500毫升二 氯甲烷中,並接著逐滴加入在200毫升二氯甲烷與150毫 升三乙胺之混合物中的66.3公克(36〇毫莫耳)N-苯基-鄰-苯二胺之溶液。當放熱反應消退時,將混合物在室溫 下再攪拌16小時。將反應混合物以500毫升IN NaOH清 洗及接著以5 00毫升水清洗兩次’經硫酸鎂乾燥且接著在 氧化鋁(鹼性,活性級1 )上以二氯甲烷層析。最後將產 φ 物從氯苯再結晶三次’在真空中乾燥且接著昇華(P=1X 10·5毫巴,T = 410°C )兩次。產率:33.8公克(31毫莫耳 ),3 1 .〇%,純度 99.9% ( HPLC )。 實例23: 9,9-雙(4,6-二苯基二啡-2-基)莽之合成法 -87- 201004904
將7.2公克( 3 00毫莫耳)氫化鈉加入在500毫升 THF中的16.6公克(100毫莫耳)莽之溶液中。在加入 ® 0.5毫升二異丙胺之後’將混合物在室溫下攪拌1小時, 接著逐滴加入58.9公克( 220毫莫耳)2 -氯-4,6 -二苯基-1,3,5 -三畊之溶液且接著將混合物在50 °C下攪拌16小時 。在冷卻之後’將混合物以加入5毫升水而中斷,在真空 中汽提出THF,將殘餘物溶解在二氯甲烷中,並將有機相 以水清洗且接著經硫酸鎂乾燥。在移除二氯甲烷之後,將 殘餘物從DMF再結晶四次,在真空中乾燥且接著昇華(
Ρ = 1χ10·5毫巴,T = 340°C )兩次。產率:17.0公克(27毫 W 莫耳),27.0%,純度 99.9% ( HPLC )。 實例 24 : 10-苯基-12,12-雙[1,1’;3,1,,]三聯苯 _5’·基- 10,12·二氫-10-氮雜茚並[2,1-b]莽之合成法 -88- 201004904
• 在 2N 3- (2-溴苯基)-N-苯基咔哩 將1.1公克(1晕莫耳)肆(三苯膦基)鈀(〇)加到 150毫升二噁烷、100毫升2_乙氧基乙醇及25〇毫升 碳酸鈉溶液中的28.7公克(1〇〇毫莫耳)N_苯基咔唑_ 3-硼酸與36_1毫升( 300毫莫耳)丨,;^二溴苯之混合物中 ’並將混合物在回流下加熱1 6小時。在冷卻之後,將有 機相分開’加入500毫升甲苯,並將混合物以5〇〇毫升水 清洗三次’經硫酸鎂乾燥,經矽膠過滴且接著在真空中從 φ 甲苯及過量1,2 -二溴苯釋出。將殘餘物以熱乙醇攪拌清洗 三次。產率:26.7公克(67毫莫耳),67.1%,根據1 H-NMR之純度97%。 b) 12,12-雙(3,5-二溴苯基)-10-苯基-10,12-二氫-10-氮 雜茚並[2,l-b]弗 將24.0毫升(60毫莫耳)正丁基鋰(在己烷中的 2.5N溶液)逐滴加到在500毫升THF中的23.9公克(60 毫莫耳)3-(2-溴苯基)-:^-苯基咔唑之冷卻至-78°(:之溶 -89- 201004904 液中,接著將混合物在-78 °C下再攪拌30分鐘,並接著逐 滴加入在100毫升THF中的38.0公克(60毫莫耳)9,9-雙(3,5-二溴苯基)荛之溶液。當加完時,允許混合物溫 熱至室溫,在真空中移除THF,將殘餘物溶解在500毫升 冰醋酸中,加入5毫升溴化氫及將懸浮液在回流下加熱半 小時。在冷卻之後,將固體以抽氣濾出,以300毫升乙醇 清洗三次且從甲苯/乙醇再結晶一次。產率:36.2公克( 45 毫莫耳),75.3%,純度約 97% (HPLC)。 c) 10-苯基-12,12-雙[l,l’;3,l”]三聯苯-5’-基-10,12-二氫-l0-氮雜茚並[2,l-b]弗 類似於實例4之製備。使用36.0公克(45毫莫耳) 12,12·雙(3,5 -二溴苯基)-10 -苯基-10,12•二氫-10 -氮雜茚 並[2,1-b]苐代替30.4公克(48毫莫耳)9,9-雙(3,5-二溴 苯基)弗。將固體從NMP再結晶三次,且在乾燥之後, 在真空中昇華(ρ=1χ10·5毫巴,T = 400°C )兩次。產率: 15.0 公克(19 毫莫耳),42.3%,純度約 99.9% (HPLC 實例25:包含根據本發明的化合物之有機電發光裝置之 生產及特徵化 根據本發明的有機電發光裝置可如例如 WO 05/003 25 3中所述方式生產。在此比較各種OLED的 結果。爲求更好的比較,故基本結構、所使用之材料、摻 -90- 201004904 雜程度及其層厚度皆相同。第一種裝置實例敘述依照先前 • 技藝之比較標準,其中發光層係由主體材料雙(9,9’_螺二 蕗-2-基)酮及客體材料(摻雜劑)lr(ppy)3所組成。此外 ,敘述各種設計的OLED,在各情況中的客體材料(摻雜 劑)爲Ir(ppy)3。具有下列結構的OLED係以類似於上述 之通用方法所生產: 電洞注射層(HIL) 20奈米之2,2’,7,7’-肆(二-對-甲 φ 苯基胺基)-螺-9,9,-二弗 電洞傳輸層(HTL) 20奈米之作爲比較之NPB ( N-萘 基-N-苯基-4,4’-二胺基聯苯)或胺 1,或化合物1 發光層(EML) 40奈米之作爲比較之主體:螺酮 (SK )(雙(9,9’-螺二莽-2-基) 酮),或化合物2 摻雜劑:Ir(ppy)3 ( %摻雜,以
φ 蒸氣沉積;其係依據 WO 04/085449 而合成) 電子導體(ETL) 20奈米之作爲比較之A1Q3 (參( 喹啉基)鋁(III)) ’或化合物3 陰極 1奈米LiF,150奈米A1於頂部 爲清楚起見,Ir(ppy)3、螺酮(SK)及胺1之結構係 描述於下。胺1在此爲依照最接近之先前技藝( JP 2005/0 85599)中的比較化合物: -91 - 201004904
根據本發明的化合物1至7係描述於下:
-92- 201004904
這些仍未最適化之oled係以標準方法特徵化;以此 目的而測定電發光光譜、從電流-電壓-發光強度特徵線( φ IUL特徵線)所計算以發光強度爲函數之效率(以Cd/A 測量)及壽命。
依照上述結構及作爲比較實驗的材料以NPB作爲電 洞傳輸材料所生產之OLED在上述條件下典型地獲得約 30 cd/A之最大效率,具有CIE : x = 〇_38,y = 0.57之色彩 座標。以1 00 0 cd/m2之參考發光密度需要4.4 V之電壓。 在1 000 cd/m2之初發光密度下的壽命爲約7700小時(參 見表1,實例26)。在其他方面相同的裝置結構中以胺1 作爲電洞傳輸材料(參見表1,實例27)獲得在41 cd/A * 93 - 201004904 之區域內的較佳最大效率’但是以1000 cd/m2之參考發 光密度需要5.3 V之電壓’且壽命只有約5600小時。 相對之下,使用根據本發明的電子阻擋材料(化合物 1)所生產之根據本發明的OLED顯出47 cd/A之顯著增 加的最大效率,具有CIE: x = 0.38,y = 0.58之色彩座標, 其中以1000 cd/m2之參考發光密度所必要之電壓爲4.4 V (參見表1,實例28)。在1000 cd/m2之初發光密度下 的7400小時壽命可與比較性實例26相近(參見表1,實 例28 )。相對於比較實驗,使用主體材料(化合物2 )代 替螺酮所生產之根據本發明的OLED (在其他方面具有相 同的結構)顯出35 cd/A之最大效率,具有CIE: χ = 0·31 ,y = 0.62之改進的色彩座標,其中以1 000 Cd/m2之參考 發光密度所必要之電壓爲5.2 V (參見表1,實例29)。 在1 000 cd/m2之初發光密度下的6900小時壽命與使用螺 嗣時相近(參見表1,實例29 )。 假設化合物1係用作電子阻擋材料及以化合物3代替 Alq用作電子傳輸材料,則獲得54 cd/A之最大效率,具 有CIE: x = 0.37’ y = 0.59之色彩座標,其中以1〇〇〇 cd/m2 之參考發光密度所必要之電壓爲4.1 V(參見表1,實例 30)。在1 000 cd/m2之初發光密度下的7200小時壽命爲 相近之値,且4.1 V之電壓小於參考材料Alq(參見表1 ,實例22)。 假設根據本發明的化合物4、5及7係用作基質材料 ,則獲得非常好的效率與好的壽命組合。化合物6尤其適 201004904 合作爲電子導體,其得到在低壓下好的效率及壽命。
表1 :以根據本發明的化合物及以Ir(ppy)3作爲摻雜劑之 裝置結果 實例 HTL/EBL 20奈米 EML 40奈米 ETL 20奈米 最大效率 [cd/A] 在1000cd/m2 下之電壓[V] CIE (x5y) 壽命[小時], 在1000cd/m2下 之初發光強度 26比較性· NPB SK: Alq 30 4.4 0.38/ 7700 Ir(ppy)3 0.57 27比較f生· 胺I SK: Alq 41 5.3 0.38/ 5600 Ir(ppy)3 0.58 28 比較性.1 SK: Alq 47 4.4 0.38/ 7400 Ir(ppy)3 0.58 29 NPB 比較性·2 Alq 35 5.2 0.31/ 6900 Ir(ppy)3 0.62 30 比較性.1 SK: 比較1生· 54 4.1 0.37/ 7200 Ir(ppy)3 3 0.59 31 NPB 比較性.4 Alq 41 5.2 0.36/ 7000 Ir(ppy)3 0.59 32 比較性.1 比較性.4 Alq 57 4.3 0.36/ 7800 Ir(ppy)3 0.59 33 比較性.1 比較性.5 Alq 61 4.5 0.36/ 7200 Ir(ppy)3 0.59 34 比較性.1 SK: 比較性. 52 4.0 0.37/ 7300 Ir(ppy)3 6 0.60 35 比較性_1 比較性_7 Alq 53 3.9 0.38/ 8100 Ir(ppy)3 0.59 -95-
Claims (1)
- 201004904 七、申請專利範園: 1· 一種式(1)化合物,其中下述適用於所使用之符號及下標: X 在各出現場合係相同或不同地爲CR1或N,其中在各 環中最多3個基團X代表N; 或兩個直接鄰接之基團X代表下列式(7)之單元❿ 其中虛線鍵表示單元與鄰接之C或N原子之鍵聯; Y 在各出現場合係相同或不同地爲單鍵或選自BR1、 C(R1)2 ' C( = 0) ' C( = NR1) > C( = C(R1)2) ' SiiR^z ' NR1、PR1、P( = 0)Ri、O、S、S( = 0)、S( = 0)2、 C^R^-CHR1):、CURl-NR1 或 CRkCR1 之基團; Z 在各出現場合係相同或不同地爲CR1或N,其中在各 環中最多2個符號Z代表N; R 在各出現場合係相同或不同地爲Cl'Br'1'三氟甲 -96- 201004904 磺酸酯、B(〇R2h、B(R2)2、B(N(R2)2)2、NAr2、 ’ N(R2)2、SiAr3、Si(R2)3、C( = 0)Ar ' C( = 0)R2、〇Ar ' OR2、SAr、SR2、S( = 0)Ar、S( = 0)R2、S( = 〇)2Ar、 S( = 〇)2R2、PAr2、P(R2)2、P( = 0)Ar2、P( = 〇)(R2)2 或 具有_5至60個芳族環原子之芳族或雜芳族環系統, 其可被一或多個基團R1取代; Ar 在各出現場合係相同或不同地爲具有5至30個芳族 φ 環原子之芳族或雜芳族環系統,其可被一或多個非芳 族基團R1取代;在此與相同的氮或磷原子鍵結的兩 個基團Ar亦可以單鍵或選自B(R2)、C(R2)2、Si(R2)2 、C = 0、C = NR2、C = C(R2)2、O、S、S = 0、S02、 N(R2)、P(R2)及P( = 〇)R2之橋互相連接; R1 在各出現場合係相同或不同地爲H、D、F' Cl、Br、 I、CHO、N(R2)2、Ν(Αγ)2、C( = 0)Ar、Ρ( = 〇)(Αγ)2、 S( = 〇)Ar、 S( = 0)2Ar、CR2 = CR2Ar、CN、N02、 • Si(R2)3、B(OR2)2、B(R2)2、b(n(r2)2)2、oso2r2 ;具 有1至40個C原子之直鏈烷基、烯基、块基、烷氧 基或硫烷氧基或具有3至40個C原子之支鏈或環狀 烷基、烯基、炔基、烷氧基或硫烷氧基,其中每個可 被一或多個基團R2取代,其中一或多個未鄰接之 CH2 基團可被 R2C=CR2、C=C、Si(R2)2、Ge(R2)2、 Sn(R2)2、C = 0、C = S ' C = Se ' C = NR2 ' P( = 〇)(R2) ' SO、S〇2、NR2、O、S或 CONR2替換,且其中一或 多個H原子可被F、Cl、Br、I、CN或N02替換;或 -97- 201004904 具有5至60個芳族環原子之芳族或雜芳族環系統, 其可在各情況中被一或多個基團R2取代;或具有5 至60個芳族環原子之芳氧基或雜芳氧基,其可被一 或多個基團R2取代;或該等系統之組合;二或多個 鄰接之取代基R1在此亦可互相形成單-或多環脂族或 芳族環系統; R2 在各出現場合係相同或不同地爲H、D或具有1至20 個C原子之脂族、芳族及/或雜芳族烴基,另外, 其中Η原子可被F替換;二或多個鄰接之取代基R2 在此亦可互相形成單-或多環脂族或芳族環系統; η 爲1或2 ; 下列的化合物係從本發明排除:2.根據申請專利範圍第1項之化合物’其爲式(2) 3) 、(8) 、(9) 、(1〇)或(11)化合物: -98 - 201004904其中所使用之符號及下標具有申請專利範圍第1項中指示 之意義。 3. 根據申請專利範圍第1或2項之化合物,其中符 號Y代表單鍵或選自(^(Ι^Η、Ο或NR1之基團。 4. 根據申請專利範圍第1或2項之化合物,其爲式 (2a) 、 (3a) 、 (8a) 、 (8b) 、 (9a) 、 (9b)、( -99- 201004904 10a) 、(10b) 、(lla)或(lib)化合物:-100- 201004904其中所使用之符號具有申請專利範圍第1項中指示之意義 〇 5.根據申請專利範圍第1或2項之化合物,其爲式 霉^ (4a)或(4b)化合物:其中所使用之符號具有申請專利範圍第1項中指示之意義 〇 6.根據申請專利範圍第1或2項之化合物,其爲式 -101 - 201004904 (4c) 、 (4d) 、 (8c) 、 (8d) 、 (9c) 、 (9d)、 10c) 、( 10d) 、( 11c)或(lid)化合物··-102- 201004904 ^其中所使用之符號及下標具有申請專利範圍第1項中指示 之意義。 7·根據申請專利範圍第1或2項之化合物,其中符 φ 號R在各出現場合係相同或不同地代表NAr2、C( = 0)Ar、 Ρ( = 〇)ΑΓ2或具有5至30個芳族環原子之芳族或雜芳族環 系統’其可被一或多個非芳族基團Rl取代。 8·根據申請專利範圍第1或2項之化合物,其中假 設基團R或R1代袠基團ν(Αγ)2,則基團R或Rl係選自 式(5)或式(6)之基團: -103- 201004904其中R2具有上述指示之意義,且: φ E 代表單鍵、0、S、N(R2)或 C(R2)2; Ar1在各出現場合係相同或不同地爲具有5至20個芳族 環原子之芳族或雜芳族環系統或具有15至30個芳族 環原子之三芳胺基團,其中每個可被一或多個基團 R2取代,較佳爲具有6至14個芳族環原子之芳基或 雜芳基或具有18至30個芳族環原子,較佳爲具有 18至22個芳族環原子之三芳胺基團,其中每個可被 一或多個基團R2取代; © P 在各出現場合係相同或不同地爲〇或1; 及/或假設基團R代表芳族或雜芳族環系統,則基團R 係選自苯基、1-萘基、2-萘基、蒽基、苯蒽基、1-或2-萘 蒽基、聯苯基、荘基、螢蒽基、2-、3-、4-、5-、6-或7-苯並蒽基、N-苯並咪唑基、苯基-N-苯並咪唑基、N-苯基 苯並咪唑基或苯基-N_苯基苯並咪唑基。 9· 一種製備根據申請專利範圍第1至8項中一或多 項之化合物的方法,其包含令雙(3,5-二溴)二苯基酮與 -104- 多項 阖第 別選 鵝( 晶體 201004904 "經取代或未經取代之2-鋰聯苯、2-錐二苯酸、2_錐 ’硫酸、2- ( 2-鋰苯基)-2-苯基-1,3.二氧戊環、錐 苯胺或對應之格任亞化合物反應’得到二方基甲醇 在酸性條件下環化及隨意地接著與溴基團進一步反 1〇. 一種含有一或多種根據申請專利範圍第1 中一或多項之化合物的二聚物、三聚物、四聚物、 、寡聚物、聚合物或樹枝狀聚合物,其中一或多 〇 或R2代表在二聚物、三聚物、四聚物或五聚物 (1 )化合物之間的鍵或從式(1 )化合物到聚合物 物或樹枝狀聚合物的鍵,或其中此鍵結係經由在基 的取代基發生。 11. 一種混合物,其包含至少一種根據申請專 第1至8或10項中一或多項之化合物與至少—種 合物。 . I2· 一種溶液,其包含至少一種根據申請專利 1至8或10項中一或多項之化合物及至少—種有 13. —種根據申請專利範圍第1至8或1〇項 之化合物的用途,其係用於電子裝置中。 M. —種電子裝置,其包含至少—種根據申請 1至8或10項中一或多項之化合物,該電子 自有機電發光裝置(0LED、pLED)、有機場 0-FET)、有機薄膜電晶體(〇_tft)、有機 (0-LET)、有機積體電路(〇 Ic)、有機太 二苯基 苯基二 ,接著 應。 至8項 五聚物 個基團 中的式 、寡聚 團R上 利範圍 另一化 範圍第 機溶劑 中一或 專利範 裝置特 效電晶 發光電 陽能電 -105- 201004904 池(O-SC) '有機場淬滅裝置(〇_FQD)、發光電化學電 池(LEC )、有機雷射二極體(〇_雷射)或有機感光器。 15·根據申請專利範圍第14項之有機電發光裝置, 其中特別假設一或多個基團R及/或R1代表C( = 0)Ar、 S( = C))Af、S( = 〇)2Ar或P( = 〇)Ar2,則根據申請專利範圍第 1 S 8 $中一或多項之化合物係用作發螢光或發磷光化合 物之基質材料’及/或其中特別假設一或多個基團R及/ 或R1代表N(Ar)2,則根據申請專利範圍第i至8項中— 或多項之化合物係用作電洞傳輸材料或電洞注射材料或電 子阻擋材料或激子阻擋材料,及/或其中特別假設基團γ 代表〇〇、P( = 〇)、SO或8〇2及/或取代基R及/或R】 少一者代表雜芳基(其代表缺電子雜環)或代表 、Ρ( = 0)Αγ2、S( = 0)Ar 或 s(0)2Ar,則根據申請專 利範圍第1至8項中一或多項之化合物係用作電子傳輸材 料或電洞阻擋材料。-106- 201004904 四、指定代表圖: (一) 、本案指定代表圖為:無 (二) 、本代表圖之元件符號簡單說明:無 201004904 五、本案若有化學式時,請揭示最能顯示發明特徵的化學 式:式(1)-4-
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2009
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- 2009-03-11 CN CN201610236009.1A patent/CN105906546B/zh active Active
- 2009-03-11 WO PCT/EP2009/001736 patent/WO2009124627A1/de active Application Filing
- 2009-03-11 KR KR1020107024955A patent/KR101578570B1/ko active IP Right Grant
- 2009-03-11 CN CN200980111846XA patent/CN101983190A/zh active Pending
- 2009-03-11 AT AT09730490T patent/ATE555092T1/de active
- 2009-03-11 EP EP09730490A patent/EP2260023B1/de active Active
- 2009-03-11 JP JP2011503351A patent/JP5653902B2/ja active Active
- 2009-03-11 CN CN201410490593.4A patent/CN104327003B/zh active Active
- 2009-04-02 TW TW098111009A patent/TW201004904A/zh unknown
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US9127017B2 (en) | 2011-05-25 | 2015-09-08 | American Dye Source, Inc. | Compounds with oxime ester and/or acyl groups |
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TWI557102B (zh) * | 2011-05-25 | 2016-11-11 | 美國染料來源公司 | 具有肟酯基及/或醯基之化合物 |
US9278927B2 (en) | 2011-08-03 | 2016-03-08 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
TWI550055B (zh) * | 2011-08-03 | 2016-09-21 | 三星顯示器有限公司 | 雜環化合物及含其之有機發光裝置 |
TWI567161B (zh) * | 2011-11-03 | 2017-01-21 | 三星顯示器有限公司 | 雜環化合物及包含其之有機發光裝置 |
Also Published As
Publication number | Publication date |
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CN104327003A (zh) | 2015-02-04 |
EP2260023B1 (de) | 2012-04-25 |
CN101983190A (zh) | 2011-03-02 |
JP5653902B2 (ja) | 2015-01-14 |
CN105906546B (zh) | 2019-02-22 |
CN104327003B (zh) | 2017-10-24 |
US8361638B2 (en) | 2013-01-29 |
KR101578570B1 (ko) | 2015-12-28 |
JP2011521894A (ja) | 2011-07-28 |
KR20100133467A (ko) | 2010-12-21 |
WO2009124627A1 (de) | 2009-10-15 |
DE102008017591A1 (de) | 2009-10-08 |
US20110037027A1 (en) | 2011-02-17 |
EP2260023A1 (de) | 2010-12-15 |
ATE555092T1 (de) | 2012-05-15 |
CN105906546A (zh) | 2016-08-31 |
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