TWI521041B - 金屬錯合物 - Google Patents
金屬錯合物 Download PDFInfo
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- TWI521041B TWI521041B TW100116507A TW100116507A TWI521041B TW I521041 B TWI521041 B TW I521041B TW 100116507 A TW100116507 A TW 100116507A TW 100116507 A TW100116507 A TW 100116507A TW I521041 B TWI521041 B TW I521041B
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- 229910052751 metal Inorganic materials 0.000 title claims description 38
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- 125000003118 aryl group Chemical group 0.000 claims description 51
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
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- 238000011282 treatment Methods 0.000 claims description 18
- 239000011159 matrix material Substances 0.000 claims description 17
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
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- 238000000034 method Methods 0.000 claims description 12
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- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-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
- 210000001835 viscera Anatomy 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Description
本發明有關例如具有經改善之溶解度的金屬錯合物、製備該等金屬錯合物之方法、包含該等金屬錯合物之裝置,和該等金屬錯合物之用途。
採用有機半導體作為功能性材料之有機電發光裝置(OLED)的結構係描述於例如US 4539507、US 5151629、EP 0676461及WO 98/27136中。此處所採用之發光材料愈來愈多是顯示磷光而非螢光之有機金屬錯合物(請參見M. A. Baldo等人之Appl. Phys. Lett. 1999,75,4-6)。由於量子力學原因,使用有機金屬化合物作為磷光發光體,能量及功率效率可能增加多達四倍。然而,通常仍需要改良顯示三重態發射之OLED,尤其是有關效率、操作電壓及使用壽命。此點在較短波範圍發射(即綠色及藍色)之OLED尤其如此。此外,許多磷光發光體不具有用於從溶液加工之適當溶解度,所以在此也進一步需要改良。
根據先前技術,磷光OLED中所使用之三重態發光體尤其是銥及鉑錯合物,其通常以環金屬化錯合物之形式使用。在此配位子經常為苯基吡啶之衍生物。然而,該等錯合物之溶解度經常是低的,使得從溶液加工更困難或完全妨礙從溶液加工。
先前技術揭示銥錯合物,其於苯基吡啶配位子之苯基環上在金屬配位之對位任意經取代之芳基或雜芳基取代(WO 2004/026886 A2)。此導致改良之錯合物溶解度。然而,在此仍需要進一步改良錯合物之溶解度及效率和使用壽命。
出乎意料地,已發現更詳細描述於下文之某些金屬鉗合錯合物具有改良之溶解度,且另外產生有機電發光裝置之改良,尤其是有關效率及使用壽命方面。本發明因此有關這些金屬錯合物且有關包含這些錯合物之有機電發光裝置。
本發明係關於式(1)化合物
M(L)n(L’)m 式(1)
其中通式(1)之化合物包含式(2)之M(L)n部分:
其中M經由X和碳原子C鍵結至任何所要之雙牙配位子L,及
其中下列定義適用於所使用之符號及標號:
M 為選自由銥、銠、鉑及鈀所組成之群組的金屬;
X 在每次出現時相同或不同地為CR1或N;
Y 在每次出現時相同或不同地為單鍵或選自下列之二價基:C(R1)2、C(=O)、O、S、SO、SO2、NR1、PR1或P(=O)R1、具有5至60個原子之脂族、芳族或雜芳族烴(其在各情況中可經一或多個R3基團取代);
R1 在每次出現時相同或不同地為H、D、F、Cl、Br、I、N(R2)2、CN、NO2、Si(R2)3、B(OR2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2、具有1至40個C原子之直鏈烷基、烷氧基或硫烷氧基或具有2至40個C原子之直鏈烯基或炔基或具有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(其中每一基團各可經一或多個R2基團取代,其中一或多個非相鄰CH2基團可經下列基團置換:R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2且其中一或多個H原子可經D、F、Cl、Br、I、CN或NO2置換)、或具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況中可經一或多個R2基團取代)、或具有5至60個芳族環原子之芳氧基或雜芳氧基(其可經一或多個R2基團取代)、或具有10至40個芳族環原子之二芳胺基、二雜芳胺基或芳基雜芳胺基(其可經一或多個R2基團取代)、或二或多個該等基團之組合;二或多個R1基團在此亦可彼此形成單環或多環之脂族、芳族及/或苯并稠合環系統;
R2 在每次出現時相同或不同地為H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、具有1至40個C原子之直鏈烷基、烷氧基或硫烷氧基或具有2至40個C原子之直鏈烯基或炔基或具有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(其中每一基團各可經一或多個R3基團取代,其中一或多個非相鄰CH2基團可經下列基團置換:R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3且其中一或多個H原子可經D、F、Cl、Br、I、CN或NO2置換)、或具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況中可經一或多個R3基團取代)、或具有5至60個芳族環原子之芳氧基或雜芳氧基(其可經一或多個R3基團取代)、或具有10至40個芳族環原子之二芳胺基、二雜芳胺基或芳基雜芳胺基(其可經一或多個R3基團取代)、或二或多個該等基團之組合;二或多個相鄰R2基團在此可彼此形成單環或多環之脂族或芳族環系統;
R3 在每次出現時相同或不同地為H、D、F或具有1至20個C原子之脂族、芳族及/或雜芳族烴基團,此外其中一或多個H原子可經F置換;二或多個R3取代基在此亦可彼此形成單環或多環之脂族或芳族環系統;
L’ 在每次出現時相同或不同地為任何所要之共配位子;
W 等於式(3)
其中環A可為任何所要的經取代或未經取代之具有5至60個原子之脂族、芳族或雜芳族環或經取代或未經取代之多環系統,其可以任何可能的方式與相鄰環縮合;
其中,在一較佳體系中,環A為式(3a)之化合物,其可以任何可能的方式與相鄰環縮合;
T、U在每次出現時相同或不同地選自由-C(R1)2、-Si(R1)2、-N、-NR1、-O、-S、-C(=O)、-S(=O)、-SO2、-CF2、-SF4、-P、-P(=O)R1、-PF2、-P(=S)R1、-As、-As(=O)、-As(=S)、-Sb、-Sb(=O)和-Sb(=S)所組成之群組;
q、r 彼此獨立為0或1;
p 大於或等於1;
t 為0、1或2;
n 在M等於銥或銠時為1、2或3且在M等於鉑或鈀時為1或2;
m 為0、1、2、3或4;
標號n和m在此係經選擇以使M等於銥或銠的金屬上之配位數相當於6且M等於鉑或鈀的金屬上之配位數相當於4;
複數個配位子L在此也可彼此連接,或L可經由任何所要的橋鍵Z連接至L’且因此形成三牙、四牙、五牙或六牙配位子系統。
在本發明之一較佳體系中,通式(1)之化合物包含式(4)至(20)之M(L)n部分
其中下列定義適用於所使用之符號及標號:
Q 在每次出現時相同或不同地為R1C=CR1、R1C=N、O、S、Se或NR1;
V 在每次出現時相同或不同地為O、S、Se、NR1或C(R1)2。
就本發明意義而言,芳基包含6至40個C原子;就本發意義的而言,雜芳基包含2至40個C原子及至少一個雜原子,其限制條件為C原子及雜原子之總和至少為5。雜原子較佳係選自N、O及/或S。芳基或雜芳基在此係用以表示單純芳族環(即苯)、或簡單雜芳族環(例如吡啶、嘧啶、噻吩、等等)、或稠合芳基或雜芳基(例如萘、蒽、菲、喹啉、異喹啉、等等)。
就本發明意義而言,芳族環系統在環系統中包含6至60個C原子。就本發明意義而言,雜芳族環系統在環系統中包含2至60個C原子及至少一個雜原子,其限制條件為C原子與雜原子之總和至少為5。雜原子較佳係選自N、O及/或S。就本發明目的而言,芳族或雜芳族環系統意欲用以表示並非必然僅含有芳基或雜芳基、而是意欲包括其中複數個芳基或雜芳基可另外藉例如像是sp3-混成之C、N或O原子或羰基基團的非芳族單元(較佳小於10%之非H的原子)所中斷之系統。因此,就本發明之目的而言,例如,系統諸如9,9’-螺二茀、9,9-二芳基茀、三芳基胺、二芳基醚、二苯乙烯、等等,也意欲表示芳族環系統,且同樣地其中二或多個芳基被例如直鏈或環狀烷基或矽烷基中斷的系統。
環狀烷基、烷氧基或硫烷氧基就本發明意義而言表示單環、雙環、多環基團。
就本發明目的而言,C1-至C40-烷基基團,其中,除此之外,個別H原子或CH2基也可經上述基團取代,用以表示例如甲基、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、第三戊基、2-戊基、環戊基、正己基、第二己基、第三己基、2-己基、3-己基、環己基、2-甲基戊基、正庚基、2-庚基、3-庚基、4-庚基、環庚基、1-甲基環己基、正辛基、2-乙基己基、環辛基、1-雙環[2.2.2]辛基、2-雙環[2.2.2]辛基、2-(2,6-二甲基)辛基、3-(3,7-二甲基)辛基、三氟甲基、五氟乙基或2,2,2-三氟乙基基團。烯基基團用以表示例如乙烯基、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、環辛烯基或環辛二烯基。炔基基團用以表示例如乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。C1-至C40-烷氧基基團用以表示例如甲氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基或2-甲基丁氧基。具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況中亦可經上述R基取代且其可經由任一所要位置鍵接至該芳族或雜芳族環系統)用以表示例如衍生自下列之基:苯、萘、蒽、苯並蒽、菲、苯並菲、芘、、苝、(fluoranthene)、苯並、稠四苯、稠五苯、苯並芘、聯苯、伸聯苯、聯三苯、伸聯三苯、茀、螺二茀、二氫菲、二氫芘、四氫芘、順-或反-茚並茀、順-或反-單苯並茚並茀、順-或反-二苯並茚並茀、三聚茚(truxene)、異三聚茚(isotruxene)、螺三聚茚、螺異三聚茚、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、啡啶、苯並-5,6-喹啉、苯並-6,7-喹啉、苯並-7,8-喹啉、啡噻、啡噁、吡唑、吲唑、咪唑、苯並咪唑、萘並咪唑(naphthimidazole)、啡咪唑(phenanthrimidazole)、吡啶並咪唑(pyridimidazole)、吡並咪唑(pyrazinimidazole)、喹噁啉並咪唑(quinoxalinimidazole)、噁唑、苯並噁唑、萘噁唑(naphthoxazole)、蒽噁唑(anthroxazole)、菲噁唑(phenanthroxazole)、異噁唑、1,2-噻唑、1,3-噻唑、苯並噻唑、嗒、苯並嗒、嘧啶、苯並嘧啶、喹噁啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮雜芘、4,5-二氮雜芘、4,5,9,10-四氮雜苝、吡、啡、啡噁、啡噻、熒紅環(fluorubin)、啶、氮雜咔唑、苯並咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯並三唑、1,2,3-噁二唑、1,2,4-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、1,2,4-三、1,2,3-三、四唑、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、嘌呤、喋啶、吲和苯並噻二唑。
式(1)之化合物可為帶電或不帶電。在一較佳體系中,式(1)之化合物為電中性。此以簡易方式達成,配位子L及L’之電荷係經選擇以補償錯合金屬原子M之電荷。
此外較佳者為式(1)之化合物,其特徵為金屬原子周圍之價電子總數對於鉑及鈀為16及對於銥或銠為18。此為較佳係因為該等金屬錯合物特別安定。
在本發明較佳體系中,M表示銥或鉑。M特佳係表示銥。
若M表示鉑或鈀,則標號n表示1或2。若標號n=1,則一個雙牙或兩個單牙配位子L’(較佳為一個雙牙配位子L’)也配位至金屬M。對應地,一個雙牙配位子L’之標號m=1,且兩個單牙配位子L’之標號m=2。若標號n=2,則標號m=0。
若M表示銥或銠,標號n表示1、2或3,較佳表示2或3和特佳表示3。若標號n=1,則四個單牙或二個雙牙或一個雙牙和二個單牙或一個三牙和一個單牙或一個四牙配位子L’(較佳為二個雙牙配位子L’)也配位至金屬。對應地,視配位子L’而定,標號m等於1、2、3或4。若標號n=2,一個雙牙或二個單牙配位子L’(較佳為一個雙牙配位子L’)也配位至金屬。對應地,視配位子L’而定,標號m等於1或2。若標號n=3,則標號m=0。
在本發明較佳體系中,符號X在每次出現時相同或不同地表示CR1。
在本發明另一較佳體系中,所有符號X在每次出現時相同或不同地表示CR1或所有符號X表示N。
在本發明另一較佳體系中,符號Q在每次出現時相同或不同地表示R1C=CR1、R1C=N、O或NR1,特佳表示R1C=CR1和R1C=N且尤佳表示R1C=CR1。
在本發明另一較佳體系中,符號V在每次出現時相同或不同地表示O、S或NR1,特佳表示S或NR1且尤佳表示S。
在本發明另一較佳體系中,符號Y表示單鍵或選自C(=O)或NR1之二價基,特佳表示單鍵。
上述較佳選擇之特佳者係同時適用。
在本發明特佳體系中,下列定義適用於所使用之符號:
M 為銥或鉑,特佳銥;
X 在每次出現時為CR1,對於所有不直接鍵結至M的位置;
Q 在每次出現時相同或不同地為R1C=CR1或R1N,特佳R1C=CR1;
V 在每次出現時相同或不同地為O、S或NR1,特佳為S;
Y 在每次出現時相同或不同地為單鍵或選自C(=O)或NR1之二價基團,特佳為單鍵。
就本發明目的而言,特佳者為式(4)和(12)之化合物。
在本發明之一特佳體系中,式(4)或(12)之部分係選自下列式(21)、(22)、(23)和(24)之部分;
本發明之一尤佳體系為式(25)之化合物。
本發明之另一尤佳體系為式(26)之化合物。
本發明之另一尤佳體系為式(27)之化合物。
本發明之另一尤佳體系為式(28)之化合物。
此外特佳者為下列化合物:
在本發明之一較佳體系中,Y係選自具有5至60個原子之芳族或雜芳族烴類的基團,其在各情況中可經一或多個R3基團取代。
Y特佳為下式(33)至(63)之化合物:
X,在此為O、S、Se、NR1、C(R1)2或S(=O)2。
虛線表示連接至W或至直接鍵結至金屬M的有機配位子之部分。
Y極佳為式(33)、(36)、(37)、(39)、(40)和(48)之化合物。
Y之另一特佳化合物為式(63)之化合物。
在本發明之一較佳體系中,W特徵在於T和U彼此獨立地選自由-C(R1)2、-N、-NR1、-O和-S所組成之群組。
W和Y之連接較佳經由環B或環C發生。若W和Y之連接經由環B發生,則下式(64)之化合物表示W之特佳體系:
式(3)之另一特佳化合物為式(65)之化合物。
若p為>1,則W和Y之連接可經由任何環B發生。特佳者為W與Y之間的連接發生於直接與C環相鄰之B環。
在本發明之一極佳體系中,r=1和p=1,和式(3)之特佳化合物為具有式(66)至(71)之化合物,
式(3)之化合物另外較佳者為下式(72)至(77)之化合物:
其中所用之符號和標號具有上述意義,特別是上述之較佳意義。
W也可經由環C連接至Y,在該情況中,環C之任何自由取代位置均適合作為連接點。在此較佳者為下列式(78)至(83)之化合物:
W之另外較佳化合物為式(84)至(89)之化合物。
式(84)至(89)之化合物為較佳,特別是,若U等於C(R1)2。
式(3)之化合物另外較佳者為下式(90)至(95)之化合物:
W之另外較佳化合物為式(96)至(101)之化合物。
式(96)至(101)之化合物為較佳,特別是,若U等於C(R1)2。
在本發明之另一較佳體系中,對於根據本發明之化合物,t=0。
將配位子L連接至一或多個另外配位子L或L’之橋聯單元Z也可存在於R1基團之一者上。在本發明較佳體系中,橋聯單元Z替代R1基團之一者存在,表示配位子具有三牙或多牙或多足(polypodal)特性。也可存在此類型之二橋聯單元Z。此導致巨環配位子形成或穴狀化合物形成。
具有多牙配位子之較佳結構為下式(102)至(109)之金屬錯合物:
其中所用之符號具有上述意義,且Z較佳表示包含1至80個選自第三、第四、第五及/或第六主族(IUPAC第13、14、15或16族)之原子的橋聯單元或表示將部分配位子L彼此共價鍵結或將L鍵結至L’的3員至6員同素環或雜環。橋聯單元Z在此亦可具有不對稱結構,即Z至L或L’之連接不需要相同。
橋聯單元Z可為中性、帶單一、雙或三個負電荷或單一、雙或三個正電荷。Z較佳為中性或帶單一負電荷或單一正電荷。Z之電荷在此較佳係依整體上形成中性錯合物的方式加以選擇。
若Z為三價基團,即將三個配位子L彼此橋連或將兩個配位子L連接至L’或將一個配位子L連接至兩個配位子L’,則Z較佳在每次出現時相同或不同地選自由下列所組成之群組:B,B(R2)-,B(C(R2)2)3,(R2)B(C(R2)2)3 -,B(O)3,(R2)B(O)3 -,B(C(R2)2C(R2)2)3,(R2)B(C(R2)2C(R2)2)3 -,B(C(R2)2O)3,(R2)B(C(R2)2O)3 -,B(OC(R2)2)3,(R2)B(OC(R2)2)3 -,C(R2),CO-,CN(R2)2,(R2)C(C(R2)2)3,(R2)C(O)3,(R2)C(C(R2)2C(R2)2)3,(R2)C(C(R2)2O)3,(R2)C(OC(R2)2)3,(R2)C(Si(R2)2)3,(R2)C(Si(R2)2C(R2)2)3,(R2)C(C(R2)2Si(R2)2)3,(R2)C(Si(R2)2Si(R2)2)3,Si(R2),(R2)Si(C(R2)2)3,(R2)Si(O)3,(R2)Si(C(R2)2C(R2)2)3,(R2)Si(OC(R2)2)3,(R2)Si(C(R2)2O)3,(R2)Si(Si(R2)2)3,(R2)Si(Si(R2)2C(R2)2)3,(R2)Si(C(R2)2Si(R2)2)3,(R2)Si(Si(R2)2Si(R2)2)3,N,NO,N(R2)+,N(C(R2)2)3,(R2)N(C(R2)2)3 +,N(C=O)3,N(C(R2)2C(R2)2)3,(R2)N(C(R2)2C(R2)2)+,P,P(R2)+,PO,PS,PSe,PTe,P(O)3,PO(O)3,P(OC(R2)2)3,PO(OC(R2)2)3,P(C(R2)2)3,P(R2)(C(R2)2)3 +,PO(C(R2)2)3,P(C(R2)2C(R2)2)3,P(R2)(C(R2)2C(R2)2)3 +,PO(C(R2)2C(R2)2)3,S+,S(C(R2)2)3 +,S(C(R2)2C(R2)2)3 +,或式(110)、式(111)、式(112)或(113)
其中虛線鍵在各情況中表示連接至部分配位子L或L’之鍵結,且A在每次出現時相同或不同地選自由單鍵、O、S、S(=O)、S(=O)2、NR2、PR2、P(=O)R2、P(=NR2)、C(R2)2C(=O)、C(=NR2)、C(=C(R2)2)、Si(R2)2或BR2所組成之群組。其他所用之符號具有上述之意義。
若Z為二價基團,即將兩配位子L彼此橋聯或使一配位子L橋聯至L’,則Z較佳在每次出現時相同或不同地選自由BR2、B(R2)2 -、C(R2)2、C(=O)、Si(R2)2、NR2、PR2、P(R2)2 +、P(=O)(R2)、P(=S)(R2)、AsR2、As(=O)(R2)、As(=S)(R2)、O、S、Se,或式(114)至(122)之單元所組成之群組:
其中虛線鍵在各情況中表示連接至部分配位子L或L’之鍵結,且其他所用之符號在各情況中具有上述之意義。
較佳配位子L’如出現於式(1)中係描於下文中。對應地,也可選擇配位子基團L’,如果它們經由橋聯單元Z鍵結至L。
配位子L’較佳為中性、單陰離子性、二陰離子性或三陰離子性配位子,特佳為中性或單陰離子性配位子。其可為單牙體、雙牙體、三牙體或四牙體,且較佳為雙牙體,即較佳係具有兩個配位部位。如上所述,配位子L’亦可經由橋連基團Z鍵結至L。
較佳中性、單牙配位子L’係選自一氧化碳、一氧化氮、烷腈(例如像是乙腈)、芳腈(例如像是苄腈)、烷異腈(例如像是甲異腈)、芳異腈(例如像是苯異腈)、胺類(例如像是三甲胺、三乙胺、啉),膦特別是鹵基膦、三烷膦、三芳膦或烷芳膦,例如像是三氟膦、三甲膦、三環己膦、三-第三丁膦、三苯膦、參(五氟苯基)膦、亞磷酸酯,例如像是亞磷酸三甲酯、亞磷酸三乙酯、胂類,例如像是三氟胂、三甲胂、三環己胂、三-第三丁胂、三苯胂、參(五氟苯基)胂、第類,例如像是三氟、三甲、三環己、三-第三丁、三苯、參(五氟苯基)、含氮雜環,例如像是吡啶、嗒、吡、嘧啶、三及碳烯類,特別是Arduengo碳烯。
較佳單陰離子性、單牙配位子L’係選自氫根、氘根、鹵根F-、Cl-、Br-及I-、烷基炔根,例如像是甲基-C≡C-、第三丁基-C≡C-、芳基炔根,例如像是,苯基-C≡C-、氰根、氰酸根、異氰酸根、硫氰酸根、異硫氰酸根、脂族或芳族醇根,例如像是甲醇根、乙醇根、丙醇根、異丙醇根、第三丁醇根、酚根、脂族或芳族硫醇根,例如像是甲硫醇根、乙硫醇根、丙硫醇根、異丙硫醇根、第三丁硫醇根、苯硫酚根、胺根例如像是二甲胺根、二乙胺根、二異丙胺根、啉根,羧酸根例如像是乙酸根、三氟乙酸根、丙酸根、苯甲酸根、芳基例如像是苯基、萘基及陰離子性含氮雜環,諸如吡咯根、咪唑根、吡唑根。該等基團中之烷基較佳為C1-C20-烷基,特佳為C1-C10-烷基,極佳係C1-C4-烷基。芳基亦用以表示雜芳基。該等基團係如前文定義。
較佳二或三陰離子性配位子係為O2-、S2-、碳化物(其導致R-C≡M形式之配位)及氮烯(其導致R-N=M形式之配位)(其中R通常表示取代基)或N3-。
較佳中性或單或二陰離子性之雙牙或多牙配位子L,係選自二胺類,例如像是乙二胺、N,N,N’,N’-四甲基乙二胺、丙二胺、N,N,N’,N’-四甲基丙二胺、順或反-二胺基環己烷、順或反-N,N,N’,N’-四甲基二胺基環己烷、亞胺類,例如像是2-[1-(苯亞胺基)乙基]吡啶、2-[1-(2-甲基苯亞胺基)乙基]吡啶、2-[1-(2,6-二異丙基苯亞胺基)乙基]吡啶、2-[1-(甲亞胺基)乙基]吡啶、2-[1-(乙亞胺基)乙基]吡啶、2-[1-(異丙亞胺基)乙基]吡啶、2-[1-(第三丁亞胺基)乙基]吡啶、二亞胺類例如像是1,2-雙(甲亞胺基)乙烷、1,2-雙(乙亞胺基)乙烷、1,2-雙(異丙亞胺基)乙烷、1,2-雙(第三丁亞胺基)乙烷、2,3-雙(甲亞胺基)丁烷、2,3-雙(乙亞胺基)丁烷、2,3-雙(異丙亞胺基)丁烷、2,3-雙(第三丁亞胺基)丁烷、1,2-雙(苯亞胺基)乙烷、1,2-雙(2-甲基苯亞胺基)乙烷、1,2-雙(2,6-二異丙基苯亞胺基)乙烷、1,2-雙(2,6-二第三丁基苯亞胺基)乙烷、2,3-雙(苯亞胺基)丁烷、2,3-雙(2-甲基苯亞胺基)丁烷、2,3-雙(2,6-二異丙基苯亞胺基)丁烷、2,3-雙(2,6-二第三丁基苯亞胺基)丁烷、含有兩個氮原子之雜環類例如像是2,2’-聯吡啶、鄰-啡啉,二膦類例如像是雙二苯膦基甲烷、雙二苯膦基乙烷、雙(二苯膦基)丙烷、雙(二苯膦基)丁烷、雙(二甲膦基)甲烷、雙(二甲膦基)乙烷、雙(二甲膦基)丙烷、雙(二乙膦基)甲烷、雙(二乙膦基)乙烷、雙(二乙膦基)丙烷、雙(二第三丁膦基)甲烷、雙(二第三丁膦基)乙烷、雙(第三丁膦基)丙烷、衍生自1,3-二酮之1,3-二酮化物例如像是乙醯丙酮、苯甲醯丙酮、1,5-二苯基乙醯丙酮、二苯甲醯甲烷、雙(1,1,1-三氟乙醯基)甲烷,衍生自3-酮酯之3-酮化物例如像是乙醯乙酸乙酯、衍生自下列胺基羧酸例如像是吡啶-2-羧酸、喹啉-2-羧酸、甘胺酸、N,N-二甲基甘胺酸、丙胺酸、N,N-二甲胺基丙胺酸之羧酸根,衍生自水楊基亞胺類例如像是甲基水楊基亞胺、乙基水楊基亞胺、苯基水楊基亞胺之水楊基亞胺根,衍生自二醇例如像是乙二醇、1,3-丙二醇之二醇根,及衍生自下列二硫醇例如像是1,2-乙二硫醇、1,3-丙二硫醇之二硫醇根。
較佳三牙配位子為含氮雜環之硼酸根,例如像是四(1-咪唑基)硼酸根及四(1-吡唑基)硼酸根。
此外特佳者為與金屬形成具有至少一個金屬-碳鍵之環金屬化五員環或六員環(特別是環金屬化五員環)的二牙單陰離子性配位子L’。這些特別是常用於有機電發光裝置之磷光金屬錯合物的領域中之配位子,也就是苯基吡啶、萘基吡啶、苯基喹啉、苯基異喹啉等等類型之配位子,其中每一配位子可經一或多個R1至R7基團取代。此類配位子之多樣性乃為熟諳磷光電發光裝置領域的技藝者所知悉,且彼等不需要進步性就能選擇更多此類型之配位子以作為式(1)之化合物的配位子L’。通常,以下式(123)至(150)表示之兩基團的組合特別適於此目的,其中之一基團經由中性氮原子或碳烯原子鍵結,而另一基團經由負電荷碳原子或負電荷氮原子鍵結。配位子L’藉由這些基團彼此鍵結則在各情況中可於標示#之位置由式(123)至(150)之基團形成。這些基團配位至金屬的位置係以*標示。這些基團也可經由一或二個橋聯單元Z而鍵結於配位子L。
此處所使用之符號具有與上述相同之意義,且較佳為各基團中最多三個符號X表示N,特佳為各基團中最多兩個符號X表示N,極佳為各基團中最多一個符號X表示N。尤佳地,所有符號X在每次出現時相同或不同地表示CR1。
在本發明一特佳體系中,式(123)至(150)之配位子L’的二個片段彼此以至少一個片段在位置*包含雜原子之方式經由位置#組合。
在本發明一極佳體系中,配位子L’係由正好一個選自式(123)至(150)的名單之沒有雜原子的片段和正好一個選自具有式(123)至(150)之片段的名單之具有雜原子(較佳為氮原子)的片段組成。
同樣較佳配位子L’為η5-環戊二烯基、η5-五甲基環戊二烯基、η6-苯或η7-環庚三烯基,其各基團可經一或多個R1基團取代。
同樣較佳配位子L’為1,3,5-順-環己烷衍生物,特別是式(150)、1,1,1-三(亞甲基)甲烷衍生物,特別是式(152)及1,1,1-三經取代甲烷,特別是式(153)和(154):
其中在各式中,已描述與金屬M之配位,R1具有上述之意義,及A在每次出現時係相同地或不同地表示O-、S-、COO-、P(R1)2或N(R1)2。
在上述結構中較佳R1基團在每次出現時係相同地或不同地選自由下列所組成之群組:H、F、Br、N(R2)2、CN、B(OR2)2、C(=O)R2、P(=O)(R2)2、具有1至10個C原子之直鏈烷基或具有2至10個C原子之烯基或炔基或具有3至10個C原子之支鏈或環狀烷基、烯基或炔基(其各基團可經一或多個R2基團取代,其中一或多個H原子可經F置換)、或具有5至14個芳族環原子之芳族環或雜芳族環系統(其在各情形中可經一或多個R2基取代);此處多個R1也可彼此形成單環或多環脂族、芳族及/或苯稠合環系統。特佳R1基團在每次出現時係相同地或不同地選自由下列所組成之群組:H、F、Br、CN、B(OR2)2、具有1至6個C原子之直鏈烷基(特別是甲基)、或具有3至10個C原子之支鏈或環狀烷基(特別是異丙基或第三丁基,其中一或多個H原子可經F置換)、或具有5至12個芳族環原子之芳族環或雜芳族環系統(其在各情況中可經一或多個R2基團取代);此處多個R1基團也可彼此形成單環或多環脂族、芳族及/或苯稠合環系統。
根據本發明之金屬錯合物原則上可藉由各種方法製備。然而,經證明下述方法特別適合。
因此本發明另關於一種製備式(1)之金屬錯合物的方法,其係藉由令對應游離配位子與式(155)之金屬烷氧化物、式(156)之金屬酮基酮鹽或式(157)之金屬鹵化物反應,
中符號M、n及R1具有上述之意義,且Hal=F、Cl、Br或I。
同樣可能使用金屬化合物,特別是帶有醇鹽及/或鹵化物及/或羥基以及酮基酮鹽基團之銥化合物。這些化合物也可帶電荷。特別適合作為起始物質之對應銥化合物係揭示於WO 04/085449號中。[IrCl2(acac)2]-,例如Na[IrCl2(acac)2]為特別適合者。
錯合物較佳如WO 02/060910號及WO 04/085449號中所述合成。雜配(heteroleptic)錯合物也可例如根據WO 05/042548號合成。合成亦可例如以熱、光化學及/或藉微波輻射活化。
這些方法能夠獲得高純度(較佳大於99%)(藉1H-NMR及/或HPLC測定)之根據本發明之式(1)化合物。
本文中所說明之合成方法尤其可製備例如下述根據本發明式(158)至(335)之化合物。
上述式(1)錯合物或上述較佳體系可用作電子裝置中的活性組分。電子裝置係表示包含陽極、陰極及至少一層的裝置,其中此層包含至少一種有機或有機金屬化合物。根據本發明之電子裝置因此包含陽極、陰極及至少一包含至少一種上述式(1)化合物的層。較佳電子裝置在本文中係選自由下列所組成之群組:有機電發光裝置(OLED、PLED)、有機積體電路(O-IC)、有機場效應電晶體(O-FET)、有機薄膜電晶體(O-TFT)、有機發光電晶體(O-LET)、有機太陽能電池(O-SC)、有機光學檢測器、有機光感受器(organic photoreceptor)、有機場淬滅裝置(O-FQD)、發光電化學電池(LEC)或有機雷射二極體(O-雷射),該電子裝置在至少一層中包含至少一種上述之式(1)化合物。特佳者為有機電發光裝置。活性組分通常為導入在陽極與陰極之間的有機或無機材料,例如電荷注入、電荷傳輸或電荷阻擋材料,但特別是發光材料及基質材料。根據本發明之化合物作為有機電發光裝置中的發光材料展現特別良好的性質。有機電發光裝置因此為本發明之較佳體系。
有機電發光裝置包含陰極、陽極及至少一發光層。除了這些發光層外,有機電發光裝置還可包含另外之層,例如,在各情況中可包含一或多層電洞注入層、電洞傳輸層、電洞阻擋層、電子傳輸層、電子注入層、激子阻擋層、電荷產生層及/或有機或無機p/n接面。在有機電發光裝置中具有例如激子阻擋功能及/或控制電荷平衡的中間層同樣地可導入於兩個發光層之間。然而,應指出的是這些層並不需要各個都存在。有機電發光裝置可包含一個發光層或數個發光層。若有數個發光層時,這些層較佳地總計具有多個在380奈米與750奈米之間的發光最大值,總體而言是產生白色發光,亦即,在發光層中使用各種能夠發螢光或磷光的發光化合物。特佳者為三層系統,其中該三層呈現藍色、綠色及橘或紅色發光(關於基本結構可參考WO 05/011013號),或包含多於三層之發光層的系統。
在本發明較佳具體係中,有機電發光裝置包含式(1)化合物或上述較佳具體係作為一或多層發光層中的發光化合物。
若使用式(1)化合物作為發光層中之發光化合物,則較佳係與一或多種基質材料組合使用。式(1)化合物及基質材料的混合物以含有發光體及基質材料之整個混合物計包含介於1和99重量%之間、較佳為介於2和40重量%之間、特佳為介於3和30重量%之間。特別是在介於5和25重量%之間的式(1)化合物。對應地,該混合物以含有發光體及基質材料之整個混合物計包含介於99和1重量%之間、較佳介於98和60重量%之間、特佳介於97和70重量%之間、特別是介於95和75重量%之間的基質材料。
適合於根據本發明化合物之基質材料為酮類、膦氧化物類及亞碸類和碸類(例如根據WO 2004/013080、WO 2004/093207、WO 2006/005627或未公開申請案DE 102008033943.1)、三芳基胺類、咔唑衍生物,例如CBP(N,N-雙咔唑基聯苯)或WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527或WO 2008/086851中所揭示之咔唑衍生物、吲哚並咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)、茚並咔唑衍生物(例如根據未公開申請案DE 102009023155.2和DE 102009031021.5)、氮雜咔唑類(例如根據EP 1617710、EP 1617711、EP 1731584、JP 2005/347160)、雙極性基質材料(例如根據WO 2007/137725)、矽烷類(例如根據WO 2005/111172)、氮雜硼雜環戊烯(azaborole)及硼酸酯(例如根據WO 2006/117052)、三衍生物(例如根據未公開申請案DE 102008036982.9、WO 2007/063754或WO 2008/056746)、鋅錯合物(例如根據EP 652273或WO 2009/062578)、二氮雜-或四氮雜矽雜環戊烯(tetraazasilole)衍生物(例如根據DE 102008056688.8)、或二氮雜磷雜環戊烯(diazaphosphole)衍生物(例如根據未公開申請案DE 102009022858.6)。
較佳者也可為採用於混合物形式之複數種不同基質材料,尤其是至少一電子傳導基質材料及至少一電洞傳導基質材料。較佳組合為例如使用芳族酮或三與三芳基胺衍生物或咔唑衍生物作為混合基質,以供根據本發明金屬之錯合物之用。較佳者同樣也為電洞傳輸材料或電子傳輸材料與不涉及電洞傳輸且亦不涉及電子傳輸之材料的混合物,如例如DE 102009014513中所揭示。
在本發明之另一較佳體系中,根據本發明之化合物可與一或多種另外發光體呈混合物使用。在此極佳者為根據本發明之化合物與一或多種螢光發光體的混合物。此外較佳者為與一或多種磷光發光體的混合物。螢光發光體主要從激發單重態發光,而磷光發光體主要從較高自旋態(例如三重態和四重態)發光。就本發明目的而言,係用有機過渡金屬之錯合物作為磷光發光體。另外發光體較佳為有機化合物。
在本發明一特佳體系中,根據本發明之化合物係與3種另外發光體混合,在特佳體系中與2種另外發光體混合且在一極佳體系中與一種另外發光體混合。
在本發明之另一較佳體系中,發光體混合物包含3種,特佳2種且極佳一種根據本發明之化合物。
在本發明一特佳體系中,發光體混合物包含正好一種根據本發明之化合物和正好一種另外發光體。
就本發明目的而言,另外較佳者為混合物的至少一種發光體之吸收光譜和至少一種其他發光體之發射光譜重疊,簡化發光體之間的能量轉移(雙摻雜)。能量轉移在此可以不同的機制發生。此非限定性實例為福斯特(Frster)或德克斯特(Dexter)能量轉移。
所述發光體混合物較佳包含至少二種皆發紅光的發光體。此外較佳者為包含至少二種皆發綠光的發光體之發光體混合物。此外較佳者為包含至少一種發紅光的發光體和至少一種發綠光的發光體之發光體混合物。
陰極較佳為包含具有低功函數之金屬、金屬合金或包含各種金屬(例如像是鹼土金屬、鹼金屬、主族金屬或鑭系元素(如Ca、Ba、Mg、Al、In、Mg、Yb、Sm、等等)的多層結構。也適當者包含鹼金屬或鹼土金屬與銀之合金,例如鎂及銀之合金。在多層結構之例子中,除了該等金屬外,也可使用具有較高功函數之其他金屬,例如像是Ag,在此情況中通常也可使用金屬之組合,例如像是Ca/Ag或Ba/Ag。較佳者也為在金屬陰極與有機半導體之間導入一具有高介電常數之材料的薄中間層。適於此目的者例如為鹼金屬或鹼土金屬氟化物,以及對應之氧化物或碳酸鹽(如LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3、等等)。此層之層厚度較佳地介於0.5與5奈米之間。
陽極較佳地包含具有高功函數之材料。陽極較佳具有相對真空大於4.5 eV之功函數。適合於此目的者一方面為具有高氧化還原電位之金屬,例如像是Ag、Pt或Au。另一方面,金屬/金屬氧化物電極(如Al/Ni/NiOx、Al/PtOx)也為較佳。對某些應用而言,為了促進有機材料之輻射(O-SC)或光線的偶合輸出(OLED/PLED、O-LASER),至少一個電極必須為透明。較佳結構使用透明陽極。較佳陽極材料在此為導電性混合金屬氧化物。特佳者為氧化銦錫(ITO)或氧化銦鋅(IZO)。此外較佳者為導電性摻雜型有機材料,特別是導電性摻雜聚合物。
通常,所有使用於根據先前技術之層的材料可使用於另一層,且熟習該技藝者將能夠將各個這些材料與根據本發明之材料組合於電子裝置而無需獨創性。
該裝置對應地(視應用而定)經結構化,提供接點且最終密封,這是因為此類型裝置的壽命在水及/或空氣存在下被大幅縮短。
此外較佳者為一種有機電發光裝置,其特徵為藉由昇華方法塗布一或多層,其中該等材料係於真空昇華單元中在低於10-5毫巴,較佳低於10-6毫巴之起始壓力下氣相沈積。起始壓力可能甚至更低,例如低於10-7毫巴。
同樣地較佳者為一種有機電發光裝置,其特徵在於一或多層係藉由OVPD(有機蒸氣相沈積)方法或借助於載體氣體昇華塗布,其中該等材料係在介於10-5毫巴和1巴之間的壓力下塗布。此方法的特殊情況為OVJP(有機蒸氣噴射印刷)方法,其中材料係經由噴嘴直接塗布且因此結構化(例如,M.S.Arnold等人之Appl. Phys. Lett. 2008,92,053301)。
此外較佳者為一種有機電發光裝置,其特徵在於一或多層係例如像是藉由旋轉塗布,或藉任何所要印刷方法(例如像是網印、柔版印刷或平版印刷,但特佳為LITI(光誘導熱成像、熱轉移印刷)或噴墨印刷)而從溶液製備。因為根據本發明之式(1)化合物在有機溶劑中具有非常好的溶解度,所以它們特別適合於從溶液處理。
有機電發光裝置也可藉由從溶液中施加一或多層及藉由蒸氣沉積作用施加一或多層其他層而以混合系統製得。因此,舉例來說,可能從溶液施加一層包含式(1)化合物與基質材料的發光層,並藉由真空蒸氣沉積作用於上施加電洞阻擋層及/或電子傳輸層。
這些方法通常為熟諳此藝者所知悉,且毫無疑問地可應用於包含式(1)化合物或上述之較佳體系的有機電發光裝置。
為了從溶液加工,式(1)化合物之溶液或調配物是必要的。較佳也可使用二或多種的溶劑混合物。適用且較佳的溶劑例如為甲苯、苯甲醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、二甲基苯甲醚、1,3,5-三甲苯、四氫萘、藜蘆素、THF、甲基-THF、THP、氯苯、二噁烷、或這些溶劑之混合物。
因此本發明此外係有關一種溶液或調配物,其包含至少一種式(1)之化合物和一或多種溶劑,特別是有機溶劑。其中可製備此類溶液之方法為熟習該項技術者已知的且描述於例如WO 02/072714、WO 03/019694和其中所引用之文獻中。
根據本發明之電子裝置,特別是有機電發光裝置以下列優於在先前技術之令人驚訝的優點區別:
1. 式(1)化合物在許多常見有機溶劑中具有極佳溶解度,因此極適合於從溶液加工。尤其,根據本發明之化合物具有高於先前技術中所述相似化合物之溶解度。
2. 包含式(1)化合物作為發光材料之有機電發光裝置具有優異之使用壽命。尤其,使用壽命優於根據先前技術之相似化合物的情形。
3. 包含式(1)化合物作為發光材料之有機電發光裝置具有優異之效率。尤其,效率優於根據先前技術之相似化合物的情形。
該等前述優點並未伴隨其他電子性質之損害。
根據本發明之化合物能夠在某些先決條件下發光。這些化合物因此用途廣泛。一些的主要應用領域在此為顯示或照明技術。另外特別有利的是將化合物和包含這些化合物之裝置使用於光電治療領域。
因此本發明此外係有關根據本發明之化合物和包含該等化合物之裝置用於治療、預防和診斷疾病之用途。本發明另外又有關根據本發明之化合物和包含該等化合物之裝置用於治療和預防美容狀況之用途。
本發明此外係有關根據本發明之化合物於製備治療、預防及/或診斷治療疾病用的裝置之用途。
許多疾病係與化妝方面有關。因此,臉上患有嚴重痤瘡之患者不僅因疾病的醫療原因和後果而更糟,且也因伴隨化妝之情況而更糟。
光電治療術或光療法是用在許多醫療及/或美容領域。根據本發明之化合物和包含這些化合物之裝置因此可用於治療及/或預防及/或診斷所有疾病,及/或習該技藝者考量使用光電治療術之美容應用。除了照射,術語光電治療術還包括光動力療法(PDT)和消毒及一般滅菌。光電治療術或光療法不僅可用於治療人類或動物,也可用於任何其他類型的生物或非生命物質。這些包括例如真菌、細菌、微生物、病毒、真核生物、原核生物、食品、飲料、水和飲用水。
術語光電治療術還包括光療法和其他類型治療的任意組合類型,例如像是以活性化合物進行治療。許多光療法具有照射或治療對象的外部,諸如對人類和動物的皮膚、傷口、黏膜、眼睛、頭髮、指甲、甲床、牙齦和舌頭部位之標的。根據本發明之治療或照射此外還可在對象內部進行,以便例如治療內臟器官(心臟、肺、等等)或血管或乳房。
根據本發明之應用的治療及/或美容領域較佳係選自皮膚疾病和皮膚相關疾病或改變或病況,例如像是牛皮癬、皮膚老化、皮膚起皺紋、皮膚再生、皮膚毛孔擴大、橘皮組織、油性/油脂性皮膚、毛囊炎、光化性角化症、癌前光化性角化症、皮膚病灶、曬傷和曬損皮膚、魚尾紋、皮膚潰瘍、痤瘡、紅斑痤瘡、粉刺造成的疤痕、痤瘡細菌、油脂性/油性分泌皮脂腺和其周圍組織之光調節、黃疸、新生兒黃疸、白斑症、皮膚癌、皮膚腫瘤、克果納傑氏症(Crigler-Najjar)、皮膚炎、異位性皮膚炎、糖尿病性皮膚潰瘍和皮膚的脫敏之群組。
就本發明目的而言特佳者為治療及/或預防牛皮癬、痤瘡、橘皮組織、皮膚起皺紋、皮膚老化、黃疸和白斑病。
對於組成物及/或包含根據本發明組成物之裝置,根據本發明之進一步應用領域係選自發炎性疾病、類風濕性關節炎、疼痛治療、創傷治療、神經疾病和病況、水腫、佩吉特氏病(Paget’s disease)、原發性和轉移腫瘤、結締組織疾病或改變、源自成哺乳動物組織中纖維母細胞之膠原蛋白、纖維母細胞和細胞量之改變、視網膜、新生血管和肥大性疾病的照射、過敏反應、呼吸道的照射、發汗、眼部新生血管性疾病、病毒感染(特別是由單純皰疹或HPV(人類乳頭狀瘤病毒)引起的感染)、用於疣和生殖器疣的治療之群組。
就本發明目的而言特佳者為治療及/或預防類風濕性關節炎、病毒感染和疼痛。
對於化合物及/或包含根據本發明化合物之裝置,根據本發明之進一步應用領域係選自冬季抑鬱症、睡眠病、改善情緒之照射、減輕疼痛(尤其是例如緊張引起的肌肉疼痛或關節疼痛)、消除關節僵硬和牙齒美白(漂白)之群組。
對於化合物及/或包含根據本發明化合物之裝置,根據本發明之進一步應用領域係選自由消毒之群組。根據本發明之化合物及/或根據本發明之裝置可用於處理為了消毒的目的之任何類型的物體(非生命物質)或對象(生命物質例如像是人類和動物)。這包括例如傷口的消毒、減少細菌、手術器械或其他物件的消毒、食品、液體(特別是水、飲用水和其他飲料)之消毒、黏膜及牙齦和牙齒之消毒。消毒在此表示減少不良作用之活微生物病原體,諸如細菌和微生物。
就上述光電治療術目的而言,包含根據本發明化合物之裝置較佳為發射具有波長介於250和1250奈米之間、特佳介於300和1000奈米之間且尤佳介於400和850奈米之間的光。
在本發明一特佳體系中,根據本發明之化合物係使用於光電治療術目的之有機發光二極體(OLED)或有機發光電化學電池(OLEC)。OLED和OLEC二者可具有平面或纖維狀結構,該平面或纖維狀結構具有任何所要截面(例如圓形、橢圓形、多邊形、方形)與單-或多層結構。這些OLEC及/或OLED可安裝在另包含機械、黏著劑及/或電子元件(例如調節照射時間、強度和波長之電池及/或控制單元)的其他裝置。這些包含根據本發明OLEC及/或OLED之裝置較佳係選自包括膏藥、護墊、膠帶、繃帶、護套、覆蓋物、帽子、睡袋、紡織品和支架之群組。
相較於先前技藝,該等裝置用於該治療及/或美容目的是特別有利的,這是因為借助於根據本發明使用OLED及/或OLEC之裝置,可能在幾乎任何地點和一天的任何時間均勻照射較低的照射強度。照射可以住院、門診及/或由病人自己進行,即由沒有醫療或美容專家開始。因此,例如膏藥可戴在衣物下,以使照射也可以在工作時間中、在休閒時間中或在睡眠中進行。複雜的住院/門診治療可在很多情況下可被避免或減少其頻率。根據本發明之裝置旨在可重複使用或為可棄式物件,其可使用一次、兩次或三次後處理掉。
進一步優於先前技藝之處為例如較低發熱和情緒方面。因此,新生兒由於黃疸治療一般必須在保溫箱中蒙住眼睛照射而沒有與父母身體上的接觸,其代表父母和新生兒的情緒緊張。借助於包含本發明之OLED及/或OLEC的本發明覆蓋物,可顯著減少情緒緊張。此外,由於相較於與習知照射設備,根據本發明之裝置產熱減少,所以小孩的更佳溫度控制是可能的。
應指出:本發明中所述之體系的變體可落在本發明的範圍內。除非明確排除,否則本說明書所述之各特徵可以用作相同、等同或類似目的之替代特徵置換。因此,除非另有說明,否則本發明中所揭示的各特徵應視為上位系列或視為等同或類似特徵的一個實例。
本發明之所有特徵可以任何方式與另一個組合,除非某些特徵及/或步驟是互相排斥。此特別適用於本發明之較佳特徵。同樣地,非必要組合中之特徵可個別地(且不以組合方式)使用。
此外應指出:許多特徵且特別是本發明之較佳體系應被視為發明本身,而非僅作為本發明體系的部分。這些特徵可被授予獨立保護,除了或替代目前主張之每項發明之外。
關於以本發明披露之技術作用的教示可予以提取和結合其他的實例。
本發明將經由下列實施例更詳細地解說,但本發明並非因此而受到限制。
實例
除非另有說明,下列合成係在保護性氣體氛圍下於無水溶劑中進行。化合物I可根據WO 2002/068435製備。化合物II、IV和VI可根據DE 102009023155製備。化合物IX可根據WO 2006/003000製備。
實例1:
化合物III之製備
製備化合物III之合成步驟:
將15.0克(16.8毫莫耳)之化合物I、38.1克(134.6毫莫耳)之化合物II和145克(685毫莫耳)之K3PO4懸浮於2100毫升之對二甲苯中。將117毫克(0.5毫莫耳)之Pd(OAc)2和6.7毫升之1M三-第三丁膦溶液加至此懸浮液。反應混合物將在回流下加熱27小時。冷卻之後,將有機相分離出來,用300毫升之水洗滌三次且隨後蒸發至乾。將殘餘物從DMSO再結晶和最後在減壓下乾燥。產率為8.5克(6.7毫莫耳),相當於理論之34%。
實例2:
化合物V之製備
製備化合物V之合成步驟:
將17.0克(190毫莫耳)之化合物I、74.2克(479毫莫耳)之化合物IV、27.2克(182毫莫耳)之碳酸鉀懸浮於350毫升之甲苯和300毫升之水中。將211毫克(0.18毫莫耳)之肆(三苯膦)鈀(0)加至此懸浮液,並將反應混合物在回流下加熱24小時。冷卻之後,將有機相分離出來,用200毫升之水洗滌三次,使用硫酸鈉乾燥且隨後蒸發至乾。將殘餘物用乙醇洗滌並從DMSO再結晶和最後在減壓下乾燥。產率為21.9克(11.2毫莫耳),相當於理論之58.7%。
實例3:
化合物VIII之製備
a)化合物VII之合成:
將22.4克(37.7毫莫耳)之化合物VI、10.5克(41.5毫莫耳)之雙(頻那醇合)二硼(bispinacolatodiboron)、9.8克(100毫莫耳)之乙酸鉀懸浮於300毫升之二噁烷中。將0.9克(1.1毫莫耳)之1,1-雙(二苯膦基)二茂鐵二氯化鈀(II)*DCM加至此懸浮液,並將反應混合物在回流下加熱8小時。冷卻之後,添加200毫升之乙酸乙酯和400毫升之水,並將有機相分離出來,用300毫升之水洗滌三次,使用硫酸鈉乾燥且隨後蒸發至乾。將殘餘物用乙醇洗滌並從乙酸乙酯再結晶和最後在減壓下乾燥。產率為19.3克(30毫莫耳),相當於理論之79.8%。
b)化合物VIII之合成
將27.2克(30.5毫莫耳)之化合物I、118.7克(185.3毫莫耳)之化合物VII、30.3克(286.6毫莫耳)之碳酸鉀懸浮於700毫升之甲苯和600毫升之水中。將290毫克(0.25毫莫耳)之肆(三苯膦)鈀(0)加至此懸浮液,並將反應混合物在回流下加熱48小時。冷卻之後,將有機相分離出來,用300毫升之水洗滌三次,使用硫酸鈉乾燥且隨後蒸發至乾。將殘餘物用乙醇洗滌並從甲苯再結晶和最後在減壓下乾燥。產率為43.6克(19.9毫莫耳),相當於理論之65.1%。
實例4:
化合物X之製備
將21.0克(23.6毫莫耳)之化合物IX、53.4克(188.4毫莫耳)之化合物II和203克(960毫莫耳)之R3PO4懸浮於3000毫升之對二甲苯中。將164毫克(0.73毫莫耳)之Pd(OAc)2和9.4毫升之1M三-第三丁基膦溶液加至此懸浮液。將反應混合物在回流下加熱42小時。冷卻之後,將有機相分離出來,用400毫升之水洗滌三次且隨後蒸發至乾。將殘餘物用乙醇洗滌和從甲苯再結晶和最後在減壓下乾燥。產率為20.6克(12.3毫莫耳),相當於理論之53%。
實例5:
化合物XI之製備
將33.8克(36.2毫莫耳)之化合物IX、141克(480毫莫耳)之化合物IV、54克(365毫莫耳)之碳酸鉀懸浮於1300毫升之甲苯和1000毫升之水中。將430毫克(0.36毫莫耳)之肆(三苯膦)鈀(0)加至此懸浮液,並將反應混合物在回流下加熱35小時。冷卻之後,將有機相分離出來,用200毫升之水洗滌三次,使用硫酸鈉乾燥且隨後蒸發至乾。將殘餘物用乙醇洗滌並從甲苯再結晶和最後在減壓下乾燥。產率為34克(16.2毫莫耳),相當於理論之44.6%。
實例6:
化合物XII之製備
將30.4克(32.6毫莫耳)之化合物IX、126.8克(293.3毫莫耳)之化合物VII、30.3克(286.6毫莫耳)之碳酸鉀懸浮於800毫升之甲苯和700毫升之水中。將290毫克(0.25毫莫耳)之肆(三苯膦)鈀(0)加至此懸浮液,並將反應混合物在回流下加熱45小時。冷卻之後,將有機相分離出來,用300毫升之水洗滌三次,使用硫酸鈉乾燥且隨後蒸發至乾。將殘餘物用乙醇洗滌並從甲苯再結晶和最後在減壓下乾燥。產率為44克(18.8毫莫耳),相當於理論之57.6%。
實例7至12:
有機電發光裝置的製造及示性
為了清楚起見,將根據本發明之化合物TE-1至TE-6、TMM-1(根據DE 102008036982.9合成)和TMM-2(根據DE 102008017591.9合成)之結構描述於下。
發光體之結構
基質結構
根據本發明之材料可從溶液使用,於其中它們產生具有良好性能的簡單裝置。該等組件之製造係根據聚合物發光二極體(PLED)之製造,其已多次描述於文獻中(例如於WO 2004/037887)。在此情況下,根據本發明之化合物TE-1至TE-4係溶於甲苯中。在此情況下,若待藉旋塗法達成之裝置的典型層厚為80奈米,則該等溶液之典型固體含量係介於16及25克/升之間。經結構化ITO基材及用於所謂緩衝層之材料(PEDOT,實際上為PEDOT:PSS)為市售品(ITO,得自Technoprint及其他公司,PEDOT:PSS為得自H.C. Starck之Clevios Baytron P水性分散液)。所使用之中間層係作為電洞注入;在此情況下,使用來自Merck之HIL-012。發射層係藉由於惰性氣體氛圍中(在此情況下為氬)藉旋塗法施加,且藉由於160℃加熱10分鐘而乾燥。最後,藉真空氣相沈積施加包含鋇及鋁之陰極。發光層及陰極之間亦可藉由氣相沈積施加電洞阻擋層及/或電子傳輸層,且該中間層亦可置換為一或多個僅具有藉由自溶液沈積發光層之後續加工步驟不會再次脫落的條件之層。該等裝置係藉標準方法示性,且所給予之OLED實例尚未最佳化。表1總結所得數據。在經處理裝置之情況下,在此顯然根據本發明之材料具有優於先前可取得者的效率及/或使用壽命。OLED在此呈現下列層結構:I)陰極(Ba/Al:3奈米/150奈米),II)發光層(80奈米;41.5重量%之TMM-1+41.5重量%之TMM-2+17重量%之TE)、III)中間層(20奈米),IV)緩衝層(80奈米;PEDOT)和V)陽極。
Claims (19)
- 一種式(1)之化合物,M(L)n(L')m 式(1)其中該化合物包含式(2)之M(L)n部分,
- 根據申請專利範圍第1項之化合物,其中該M(L)n部分係選自具有式(4)至(20)之化合物的群組
- 根據申請專利範圍第1項之化合物,其中該M(L)n部分係選自式(4)、(9)、(12)和(18)
- 根據申請專利範圍第1項之化合物,其中該M(L)n部分係選自式(4)和(12)
- 根據申請專利範圍第1項之化合物,其中對於所有不直接鍵結於M之原子,符號X在每次出現時表示CR1。
- 根據申請專利範圍第1項之化合物,其中該M(L)n部分係選自式(25)至(28)
- 根據申請專利範圍第1項之化合物,其中W係選自式(66)至(71)和(78)至(89)之化合物
- 根據申請專利範圍第1項之化合物,其中Y在每次出現時相同或不同地為單鍵或具有5至60個原子之脂族、芳族或雜芳族烴,其在各情況中可經一或多個R3基團取代。
- 根據申請專利範圍第1項之化合物,其中該Y基團係選自式(33)至(63)之化合物
- 一種製備根據申請專利範圍第1至9項中一或多項之化合物的方法,其係藉由令對應之游離配位子與式(155)之金屬烷氧化物、與式(156)之金屬酮基酮酸鹽或與式(157)之金屬鹵化物進行反應來進行:
- 一種調配物,其包含至少一種根據申請專利範圍第1至9項中一或多項之化合物,和至少一種溶劑。
- 一種如申請專利範圍第1至9項中一或多項之化合物用於電子裝置之用途。
- 根據申請專利範圍第12項之用途,其中該電子裝置係選自下列所組成之群組:有機電發光裝置(OLED、PLED)、有機積體電路(O-IC)、有機場效應電晶體(O-FET)、有機薄膜電晶體(O-TFT)、有機發光電晶體(O-LET)、有機太陽能電池(O-SC)、有機光學偵測器、有機光感受器(organic photoreceptor)、有機場淬滅裝置(O-FQD)、發光電化學電池(LEC)或有機雷射二極體(O-雷射)。
- 一種電子裝置,其包含至少一種根據申請專利範圍第1至9項中一或多項之化合物。
- 根據申請專利範圍第14項之電子裝置,其係選自下列所組成之群組:有機電發光裝置(OLED、PLED)、有機積體電路(O-IC)、有機場效應電晶體(O-FET)、有機薄膜電晶體(O-TFT)、有機發光電晶體(O- LET)、有機太陽能電池(O-SC)、有機光學偵測器、有機光感受器、有機場淬滅裝置(O-FQD)、發光電化學電池(LEC)或有機雷射二極體(O-雷射)。
- 根據申請專利範圍第14項之電子裝置,其中該電子裝置為有機電發光裝置,在該有機電發光裝置中係用根據申請專利範圍第1至9項中一或多項之化合物作為一或多個發光層中的發光化合物。
- 根據申請專利範圍第16項之電子裝置,其中該電子裝置為有機電發光裝置,在該有機電發光裝置中係用根據申請專利範圍第1至9項中一或多項之化合物作為一或多個發光層中的發光化合物且與基質材料組合。
- 根據申請專利範圍第17項之電子裝置,其中該基質材料係選自下列所組成之群組:酮類、膦氧化物類、亞碸類、碸類、三芳基胺類、咔唑衍生物、吲哚並咔唑衍生物、茚並咔唑衍生物、氮雜咔唑衍生物、雙極性基質材料、矽烷類、氮雜硼雜環戊烯(azaborole)類、硼酸酯類、三衍生物、鋅錯合物、二氮雜-或四氮雜矽雜環戊烯(tetraazasilole)衍生物或二氮雜磷雜環戊烯(diazaphosphole)衍生物、或這些基質材料之混合物。
- 根據申請專利範圍第14至18項中任一項之裝置,其係用於治療、預防及/或診斷疾病及/或美容相關狀況。
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DE102010027218A1 (de) * | 2010-07-15 | 2012-01-19 | Merck Patent Gmbh | Organische Komplexe enthaltend Metalle |
JP5707818B2 (ja) * | 2010-09-28 | 2015-04-30 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、表示素子、照明装置及び金属錯体化合物 |
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- 2011-04-20 WO PCT/EP2011/002025 patent/WO2011141120A1/de active Application Filing
- 2011-04-20 EP EP11715672.9A patent/EP2569323B1/de active Active
- 2011-04-20 CN CN201610217543.8A patent/CN105837640A/zh active Pending
- 2011-04-20 CN CN201180024028.3A patent/CN102892772B/zh active Active
- 2011-04-20 US US13/697,629 patent/US8779176B2/en active Active
- 2011-04-20 KR KR1020127032536A patent/KR101882168B1/ko active IP Right Grant
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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TWI750213B (zh) * | 2016-08-30 | 2021-12-21 | 德商麥克專利有限公司 | 金屬錯合物 |
Also Published As
Publication number | Publication date |
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EP2569323B1 (de) | 2015-02-25 |
JP2016104733A (ja) | 2016-06-09 |
DE102010020567A1 (de) | 2011-11-17 |
WO2011141120A1 (de) | 2011-11-17 |
JP5847806B2 (ja) | 2016-01-27 |
CN102892772A (zh) | 2013-01-23 |
KR20130079433A (ko) | 2013-07-10 |
EP2569323A1 (de) | 2013-03-20 |
US8779176B2 (en) | 2014-07-15 |
KR101882168B1 (ko) | 2018-07-26 |
CN105837640A (zh) | 2016-08-10 |
JP2013533214A (ja) | 2013-08-22 |
CN102892772B (zh) | 2016-05-04 |
TW201213496A (en) | 2012-04-01 |
US20130065873A1 (en) | 2013-03-14 |
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