TW202223066A - 用於有機電致發光裝置之材料 - Google Patents
用於有機電致發光裝置之材料 Download PDFInfo
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- TW202223066A TW202223066A TW110130125A TW110130125A TW202223066A TW 202223066 A TW202223066 A TW 202223066A TW 110130125 A TW110130125 A TW 110130125A TW 110130125 A TW110130125 A TW 110130125A TW 202223066 A TW202223066 A TW 202223066A
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- 239000000463 material Substances 0.000 title claims description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 125000003118 aryl group Chemical group 0.000 claims description 111
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- -1 heteroaliphatic Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
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- 238000000746 purification Methods 0.000 description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
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- 239000003054 catalyst Substances 0.000 description 4
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- 238000002347 injection Methods 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
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- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
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- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 3
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- 229960005544 indolocarbazole Drugs 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
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- 150000003248 quinolines Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 2
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- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- 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
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/225—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a condensed ring system
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/62—Purification of melamine
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract
本發明係關於適用於電子裝置之化合物,以及關於包含這些化合物之電子裝置,尤其是有機電致發光裝置。
Description
本發明係關於電子裝置,尤其是有機電致發光裝置,其包含聯伸三苯衍生物。
用於有機電致發光裝置(OLED)的發光材料通常是磷光有機金屬錯合物。一般而言,對於OLED的改良仍有需求,尤其是亦在展現三重態發射(磷光)的OLED中,例如關於效率、操作電壓及壽命方面。磷光OLED之性質不只由所使用之三重態發射體決定。更特別地,所使用的其他材料(諸如基質材料或電荷傳輸材料)在此處亦是特別重要的。這些材料的改良亦可因此使OLED性質得以改善。用於OLED的合適基質材料係例如在例如WO 2011/137157或WO 2012/048781中所揭示之聯伸三苯衍生物。
本發明之目的是提供適合用於OLED中之化合物,尤其是作為磷光發射體的基質材料或作為電洞傳輸材料,並且在其中得到經改良的性質。本發明之另一個目的是提供用於有機電致發光裝置之其他有機半導體,因而使所屬技術領域中具有通常知識者能夠有更多可能的材料選擇來生產OLED。
已令人驚訝地發現,此目的係藉由下文詳細描述之非常適用於OLED的特定化合物來實現。這些OLED尤其具有更長的壽命、經改良的效率及相對較低的操作電壓。因此,本發明提供這些化合物及包含這些化合物之電子裝置,尤其是有機電致發光裝置。
本發明提供式(1)之化合物
其中R基團亦可能出現多於一次且所使用的符號係:
Z 係O或S;
R* 係下列式(2)或(3)之基團,其中虛線鍵表示至式(1)之基本骨架的鍵,
X 在各情況下係相同或不同,且係CR或N,其中不多於二個X基團係N,或二個相鄰X基團係下列式(4)或(5)之基團:
其中虛線鍵表示式(2)中該基團之鍵聯;
Y 在各情況下係相同或不同,且係CR或N;
W 在各情況下係相同或不同,且係NAr
2、O、S或C(R)
2;
L 係單鍵或芳族或雜芳族環系統,其具有5至24個芳族環原子且可經一或多個R基團取代;
A
1、Ar
2在各情況下係相同或不同,且係芳族或雜芳族環系統,其具有5至40個芳族環原子且可經一或多個R基團取代;
R 在各情況下係相同或不同,且係H;D;F;Cl;Br;I;CN;NO
2;OR
1;SR
1;COOR
1;C(=O)N(R
1)
2;Si(R
1)
3;B(OR
1)
2;C(=O)R
1;P(=O)(R
1)
2;S(=O)R
1;S(=O)
2R
1;OSO
2R
1;具有1至20個碳原子之直鏈烷基或具有2至20個碳原子之烯基或炔基或具有3至20個碳原子之支鏈或環狀烷基,其中該烷基、烯基或炔基在各情況下可經一或多個R
1基團取代,其中一或多個非相鄰CH
2基團可經Si(R
1)
2、C=O、NR
1、O、S或CONR
1置換;或芳族或雜芳族環系統,其具有5至60個芳族環原子、較佳係5至40個芳族環原子,且在各情況下可經一或多個R
1基團取代;同時,二個R基團一起亦可形成脂族、雜脂族、芳族或雜芳族環系統;
R
1在各情況下係相同或不同,且係H;D;F;Cl;Br;I;CN;NO
2;OR
2;SR
2;Si(R
2)
3;B(OR
2)
2;C(=O)R
2;P(=O)(R
2)
2;S(=O)R
2;S(=O)
2R
2;OSO
2R
2;具有1至20個碳原子之直鏈烷基或具有2至20個碳原子之烯基或炔基或具有3至20個碳原子之支鏈或環狀烷基,其中該烷基、烯基或炔基可各自經一或多個R
2基團取代,其中一或多個非相鄰CH
2基團可經Si(R
2)
2、C=O、NR
2、O、S或CONR
2置換,且其中在該烷基、烯基或炔基中之一或多個氫原子可經D、F、Cl、Br、I或CN置換;或芳族或雜芳族環系統,其具有5至40個芳族環原子,且在各情況下可經一或多個R
2基團取代;同時,二或更多個R
1基團一起亦可形成脂族環系統;
R
2在各情況下係相同或不同,且係H、D、F、CN或具有1至20個碳原子之脂族、芳族或雜芳族有機基團,尤其係烴基基團,其中一或多個氫原子亦可經F置換。
若二個相鄰X基團係式(4)或(5)中之一者,則式(2)中其餘X基團係相同或不同且係CR或N。
在本發明的上下文中之芳基含有6至40個碳原子;在本發明的上下文中之雜芳基含有2至40個碳原子及至少一個雜原子,其先決條件為碳原子與雜原子之總和係至少5。雜原子較佳係選自N、O及/或S。在此,芳基或雜芳基係理解為意指簡單的芳族環(亦即苯)、或簡單的雜芳族環(例如吡啶、嘧啶、噻吩等)、或縮合(稠合)芳基或雜芳基(例如萘、蒽、菲、喹啉、異喹啉等)。相反地,藉由單鍵彼此連接的芳族系統(例如聯苯)則不稱為芳基或雜芳基而是芳族環系統。
在本發明的上下文中,芳族環系統在環系統中含有6至60個碳原子、較佳係6至40個碳原子。在本發明的上下文中,雜芳族環系統在環系統中含有2至60個碳原子、較佳係2至40個碳原子、及至少一個雜原子,其先決條件為碳原子與雜原子之總和係至少5。雜原子較佳係選自N、O及/或S。這些同樣應理解為意指二或多個芳基或雜芳基係彼此直接連接之系統,例如聯苯、聯三苯、聯吡啶或苯基吡啶。例如,在本發明的上下文中,諸如茀或9,9’-螺聯茀的系統亦應被視為芳族環系統。
在本發明的上下文中,用語「烷基」係用作直鏈、支鏈及環狀烷基的總稱。類似地,用語「烯基」及「炔基」分別用作直鏈、支鏈及環狀烯基及炔基的總稱。
在本發明的上下文中,脂族烴基、或烷基、或烯基、或炔基(其可含有1至40個碳原子且其中個別氫原子或CH
2基團亦可經上述基團取代)較佳係理解為意指甲基、乙基、正丙基、異丙基、正丁基、異丁基、二級丁基、三級丁基、2-甲基丁基、正戊基、二級戊基、新戊基、環戊基、正己基、新己基、環己基、正庚基、環庚基、正辛基、環辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、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、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。具有1至40個碳原子之烷氧基OR
1較佳係理解為意指甲氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基、三級丁氧基、正戊氧基、二級戊氧基、2-甲基丁氧基、正己氧基、環己氧基、正庚氧基、環庚氧基、正辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基及2,2,2-三氟乙氧基。具有1至40個碳原子之烷硫基(thioalkyl)SR
1係理解為意指尤其是甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、二級丁硫基、三級丁硫基、正戊硫基、二級戊硫基、正己硫基、環己硫基、正庚硫基、環庚硫基、正辛硫基、環辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、環戊烯硫基、己烯硫基、環己烯硫基、庚烯硫基、環庚烯硫基、辛烯硫基、環辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。一般而言,根據本發明之烷基、烷氧基或烷硫基可係直鏈、支鏈或環狀的,其中一或多個非相鄰CH
2基團可經上述基團置換;此外,一或多個氫原子亦可經D、F、Cl、Br、I、CN或NO
2置換,較佳係F、Cl或CN,更佳係F或CN。
具有5至60個芳族環原子且在各情況下可經上述R
2基團或烴基取代且可經由任何所欲的位置連接至芳族或雜芳族系統之芳族或雜芳族環系統係理解為意指尤其是衍生自下列者之基團:苯、萘、蒽、苯并蒽、菲、芘、、苝、丙二烯合茀(fluoranthene)、稠四苯、稠五苯、苯并芘、聯苯、聯伸苯、聯三苯(terphenyl)、聯伸三苯、茀、螺聯茀、二氫菲、二氫芘、四氫芘、順-或反-茚并茀、順-或反-茚并咔唑、順-或反-吲哚并咔唑、參茚并苯(truxene)、異參茚并苯(isotruxene)、螺參茚并苯、螺異參茚并苯、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻、啡㗁、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡并咪唑、喹㗁啉并咪唑、㗁唑、苯并㗁唑、萘并㗁唑、蒽并㗁唑、菲并㗁唑、異㗁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒、六氮雜聯伸三苯、苯并嗒、嘧啶、苯并嘧啶、喹㗁啉、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、啡㗁、啡噻、螢紅環(fluorubine)、啶、氮雜咔唑、苯并咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-㗁二唑、1,2,4-㗁二唑、1,2,5-㗁二唑、1,3,4-㗁二唑、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、吲及苯并噻二唑、或衍生自這些系統之組合的基團。
R*基團,亦即式(2)或(3)之基團,可鍵結至沒有Z基團鍵結的環上,從而得到下式(6)之化合物,或可鍵結至與Z基團相同的環上,從而得到下式(7)之化合物:
其中R基團亦可能出現多於一次且所使用的符號上文所給的定義。
特佳者係式(6a)及(7a)之化合物,尤其是式(6a)之化合物。
在上文及下文所述之化合物的較佳實施例中,Z係O。
在其他較佳實施例中,化合物可經部分或完全氘化。這與化合物之聯伸三苯基本骨架及取代基R及R*兩者有關。與未經氘化之化合物相比,化合物的部分或完全氘化可使裝置壽命得到改善。
在本發明之其他較佳實施例中,式(1)之化合物或其他較佳實施例之化合物含有不多於二個取代基R,該取代基R是H及D以外的基團,且更佳地不多於一個取代基R,該取代基R是H及D以外的基團。H及D以外之取代基R在此較佳地鍵結至與R*基團不同的環。特佳者係下列式(6a-1)至(7b-4)之化合物:
其中所使用的符號具有上文所給的定義。
以下描述R*之較佳實施例,亦即,式(2)及(3)之較佳基團。
在本發明之較佳實施例中,L基團係單鍵或二價芳族或雜芳族環系統,其具有6至18個芳族環原子且可經一或多個取代基R、較佳係非芳族取代基R取代。更佳地,L係單鍵或芳族環系統,其具有6至12個芳族環原子且可經一或多個較佳係非芳族R基團取代。最佳地,L係單鍵或鄰-、間-或對-鍵結的伸苯基。
更佳地,L係單鍵或隨意地係經取代伸苯基,亦即,式(L-1)至(L-3)、尤其是(L-1)或(L-2)之基團。
在式(2)之較佳實施例中,不多於一個X基團係N。更佳地,所有X基團在各情況下均相同或不同且係CR,或者二個相鄰X基團係式(4)之基團,而其他二個X基團在各情況下係相同或不同且係CR。
當二個相鄰X基團係式(4)或(5)之基團時,較佳地不多於一個Y基團係N。更佳地,Y基團在各情況下係相同或不同且係CR。
進一步較佳地,式(4)之基團中的W係NAr
2或CR
2。當W係NAr
2時,Ar
2較佳係具有6至24個芳族環原子之芳族或雜芳族環系統,較佳地係具有6至12個芳族環原子之芳族環系統,其等之各者可經一或多個R基團取代,但較佳係未經取代。
特佳者係下列式(2a)或(2a-1)之基團。
在式(3)之較佳實施例中,Ar
1在各情況下係相同或不同,且係芳族或雜芳族環系統,其具有6至30個芳族環原子且可經一或多個R基團取代,其中R基團較佳係非芳族。更佳地,Ar
1在各情況下係相同或不同,且係芳族或雜芳族環系統,其具有6至24個芳族環原子,尤其是6至13個芳族環原子,且可經一或多個較佳係非芳族R基團取代。當Ar
1係雜芳基,尤其是三、嘧啶、喹唑啉或咔唑時,較佳者亦可係該雜芳基上之芳族或雜芳族取代基R。合適的芳族或雜芳族環系統Ar
1在各情況下係相同或不同,且係選自由下列所組成之群組:苯基、聯苯(尤其是鄰-、間-或對-聯苯)、聯三苯(尤其是鄰-、間-或對-聯三苯、或支鏈聯三苯)、聯四苯(尤其是鄰-、間-或對-聯四苯、或支鏈聯四苯)、可經由1、2、3或4位置連接之茀、可經由1、2、3或4位置連接之螺聯茀、可經由1或2位置連接之萘、吲哚、苯并呋喃、苯并噻吩、可經由1、2、3或4位置連接之咔唑、可經由1、2、3或4位置連接之二苯并呋喃、可經由1、2、3或4位置連接之二苯并噻吩、茚并咔唑、吲哚并咔唑、吡啶、嘧啶、吡、嗒、三、喹啉、喹唑啉、苯并咪唑、菲、聯伸三苯或這些基團中之二或三者之組合,其各者可經一或多個R基團、較佳係非芳族R基團取代。當Ar
1係雜芳基,尤其是三、嘧啶、喹唑啉或咔唑時,較佳者亦可係該雜芳基上之芳族或雜芳族R基團。
Ar
1在此在各情況下較佳係相同或不同,且係選自下列式Ar-1至Ar-83之群組:
其中R係如上所定義,虛線鍵表示至氮原子的鍵,並且此外:
Ar
3在各情況下係相同或不同,且係二價芳族或雜芳族環系統,其具有6至18個芳族環原子且在各情況下可經一或多個R基團取代;
A
1在各情況下係相同或不同,且係NR、O、S或C(R)
2;
n 係0或1,其中n=0意指在該位置處沒有A
1基團鍵結,而R基團係鍵結至對應的碳原子;
m 係0或1,其中m=0意指Ar
4基團不存在,並且對應的芳族或雜芳族基團係直接鍵結至氮原子。
二芳基胺上特佳的Ar
1基團係Ar-1、Ar-2、Ar-3、Ar-4、Ar-13基團,其中A
1=O或S,m=1且Ar
3=對伸苯基;Ar-13,其中m=0且A
1=C(CH
3)
2或C(C
6H
5)
2;Ar-14,其中m=0且A
1=C(CH
3)
2或C(C
6H
5)
2;Ar-15,其中A
1=N-苯基,m=1且Ar
3=間-或對-伸苯基;Ar-16,其中m=0且A
1=O、S、C(CH
3)
2或C(C
6H
5)
2;Ar-43、Ar-45及Ar-46;尤其是下列基團:Ar-1a、Ar-2a、Ar-3a、Ar-4a、Ar-13a,其中A
1=O或S;Ar-13b,其中A
1=C(CH
3)
2或C(C
6H
5)
2;Ar-14a,其中A
1=C(CH
3)
2或C(C
6H
5)
2;Ar-15a、Ar-15b、Ar-16a,其中A
1=O、S、C(CH
3)
2或C(C
6H
5)
2;Ar-43a、Ar-45a及Ar-46a,
其中所使用的符號具有上文所給的定義。
以下描述本發明之化合物中之較佳取代基R、R
1及R
2。在本發明之特佳實施例中,下文對於R、R
1及R
2所指明之偏好同時發生並且適用於式(1)之結構以及上文詳述的所有較佳實施例。
在本發明之較佳實施例中,R在各情況下係相同或不同,且係選自由下列所組成之群組:H、D、F、CN、OR
1、具有1至10個碳原子之直鏈烷基或具有2至10個碳原子之烯基或具有3至10個碳原子之支鏈或環狀烷基(其中該烷基或烯基可各自經一或多個R
1基團取代,但較佳係未經取代,且其中一或多個非相鄰CH
2基團可經O置換)、或芳族或雜芳族環系統(其具有6至30個芳族環原子且在各情況下可經一或多個R
1基團取代);同時,二個R基團一起亦可形成脂族、芳族或雜芳族環系統。更佳地,R在各情況下係相同或不同,且係選自由下列所組成之群組:H、具有1至6個碳原子(尤其是具有1、2、3或4個碳原子)之直鏈烷基、或具有3至6個碳原子之支鏈或環狀烷基(其中該烷基在各情況下可經一或多個R
1基團取代,但較佳係未經取代)、或芳族或雜芳族環系統(其具有6至24個芳族環原子且在各情況下可經一或多個R
1基團、較佳係非芳族R
1基團取代)。最佳地,R在各情況下係相同或不同,且係選自由下列所組成之群組:H、D、或芳族或雜芳族環系統,其具有6至24個芳族環原子且在各情況下可經一或多個R
1基團、較佳係非芳族R
1基團取代。
此處鍵結至聯伸三苯基本骨架或Ar
1之取代基R在各情況下較佳係相同或不同,且係選自由下列所組成之群組:H、D、及芳族環系統,其具有6至24個芳族環原子,更佳係6至12個芳族環原子,且可經一或多個非芳族R
1基團取代,但較佳係未經取代。更佳地,鍵結至聯伸三苯基本骨架或Ar
1之取代基R係H或D,尤其是H。
此外,鍵結至式(3)之基團的取代基R較佳地在各情況下係相同或不同,且係選自由下列所組成之群組:H、D、芳族環系統(其具有6至24個芳族環原子、更佳係6至12個芳族環原子,且可經一或多個非芳族R
1基團取代,但較佳係未經取代)、及雜芳族環系統(其具有6至13個芳族環原子且可經一或多個R
1基團取代,其中R
1在此也可較佳地係芳族環系統)。
合適的芳族或雜芳族環系統R係選自苯基、聯苯(尤其是鄰-、間-或對-聯苯)、聯三苯(尤其是鄰-、間-或對-聯三苯、或支鏈聯三苯)、聯四苯(尤其是鄰-、間-或對-聯四苯、或支鏈聯四苯)、可經由1、2、3或4位置連接之茀、可經由1、2、3或4位置連接之螺聯茀、可經由1或2位置連接之萘、吲哚、苯并呋喃、苯并噻吩、可經由1、2、3或4位置連接之咔唑、可經由1、2、3或4位置連接之二苯并呋喃、可經由1、2、3或4位置連接之二苯并噻吩、茚并咔唑、吲哚并咔唑、吡啶、嘧啶、吡、嗒、三、喹啉、喹唑啉、苯并咪唑、菲、聯伸三苯或這些基團中之二或三者之組合,其各者可經一或多個R
1基團取代。當R係雜芳基,尤其是三、嘧啶、喹唑啉或咔唑時,較佳者亦可係該雜芳基上之芳族或雜芳族R
1基團。
當彼等係芳族或雜芳族環系統時,R基團在此較佳係選自下列式R-1至R-83之基團:
其中R
1具有上文所給的定義,虛線鍵表示至基團的鍵之位置,並且此外:
Ar
3在各情況下係相同或不同,且係二價芳族或雜芳族環系統,其具有6至18個芳族環原子且在各情況下可經一或多個R
1基團取代;
A
1在各情況下係相同或不同,且係C(R
1)
2、NR
1、O或S;
n 係0或1,其中n=0意指在該位置處沒有A
1基團鍵結,而R
1基團則係鍵結至對應的碳原子;
m 係0或1,其中m=0意指Ar
3基團不存在;其先決條件為當該等基團係Ar’之實施例時,對於結構(R-12)、(R-17)、(R-21)、(R-25)、(R-26)、(R-30)、(R-34)、(R-38)及(R-39),m=1。
當上述用於Ar
1之Ar-1至Ar-83基團及用於R之R-1至R-83基團具有二或更多個A
1基團時,其等之可能選擇包括來自A
1之定義的所有組合。在那種情況下之較佳實施例係其中一個A
1基團係NR或NR
1且另一個A
1基團係C(R)
2或C(R
1)
2、或其中二個A
1基團皆係NR或NR
1、或其中二個A
1基團皆係O者。在本發明之特佳實施例中,在具有二或更多個A
1基團之Ar或R基團中,至少一個A
1基團係C(R)
2或C(R
1)
2、或係NR或NR
1。
當Ar
1係NR或NR
1時,鍵結至氮原子之取代基R或R
1較佳係芳族或雜芳族環系統,其具有5至24個芳族環原子且亦可經一或多個R
1或R
2基團取代。在特佳實施例中,此R或R
1取代基在各情況下係相同或不同,且係芳族或雜芳族環系統,其具有6至24個芳族環原子,較佳係6至12個芳族環原子,並且不具有任何稠合芳基或雜芳基,其中二或更多個芳族或雜芳族6員環基團彼此直接稠合,且在各情況下亦可經一或多個R
1或R
2基團取代。特佳者係具有如上所述對於Ar-1至Ar-11或R-1至R-11所列之鍵結圖案的苯基、聯苯、聯三苯及聯四苯,其中這些結構可經一或多個R
1或R
2基團取代,但較佳係未經取代。
當A
1係C(R)
2或C(R
1)
2時,鍵結至該碳原子之取代基R或R
1在各情況下較佳係相同或不同,且係具有1至10個碳原子之直鏈烷基、或具有3至10個碳原子之支鏈或環狀烷基、或具有5至24個芳族環原子且亦可經一或多個R
1或R
2基團取代之芳族或雜芳族環系統。最佳地,R或R
1係甲基或苯基。在此情況下,R或R
1基團亦可一起形成環系統,而得到螺環系統(spiro system)。
在本發明之一個實施例中,至少一個R基團係富電子(electron-rich)雜芳族環系統。該富電子雜芳族環系統較佳係選自上述R-13至R-42基團,其中在R-13至R-16、R-18至R-20、R-22至R-24、R-27至R-29、R-31至R-33及R-35至R-37基團中,至少一個A
1基團係NR
1,其中R
1較佳係芳族或雜芳族環系統,尤其是芳族環系統。特佳者係R-15基團,其中m=0且A
1=NR
1。
在本發明之其他實施例中,至少一個R基團係缺電子(electron-deficient)雜芳族環系統。該缺電子雜芳族環系統較佳係選自上述R-47至R-50、R-57、R-58及R-76至R-83基團。
在本發明之其他較佳實施例中,R
1在各情況下係相同或不同,且係選自由下列所組成之群組:H、D、F、CN、OR
2、具有1至10個碳原子之直鏈烷基或具有2至10個碳原子之烯基或具有3至10個碳原子之支鏈或環狀烷基(其中該烷基或烯基在各情況下可經一或多個R
2基團取代,且其中一或多個非相鄰CH
2基團可經O置換)、或芳族或雜芳族環系統(其具有6至30個芳族環原子且在各情況下可經一或多個R
2基團取代);同時,二或更多個R
1基團一起可形成脂族環系統。在本發明之特佳實施例中,R
1在各情況下係相同或不同,且係選自由下列所組成之群組:H、具有1至6個碳原子(尤其是具有1、2、3或4個碳原子)之直鏈烷基、或具有3至6個碳原子之支鏈或環狀烷基(其中該烷基可經一或多個R
2基團取代,但較佳係未經取代)、或芳族或雜芳族環系統(其具有6至24個芳族環原子且在各情況下可經一或多個R
2基團取代,但較佳係未經取代)。
在本發明之其他較佳實施例中,R
2在各情況下係相同或不同,且係H、F、具有1至4個碳原子之烷基或具有6至10個碳原子之芳基(其可經具有1至4個碳原子之烷基取代,但較佳係未經取代)。
同時,藉由真空蒸發處理的本發明之化合物中的烷基較佳地具有不多於5個碳原子、更佳地不多於4個碳原子、最佳地不多於1個碳原子。對於由溶液加工之化合物,合適的化合物亦係那些經烷基取代者,尤其是具有至多10個碳原子之支鏈烷基,或係那些經寡聚伸芳基取代者,例如鄰-、間-或對-聯三苯或支鏈聯三苯或聯四苯基團。
當式(1)之化合物或較佳實施例之化合物用作磷光發射體之基質材料或用於直接鄰接磷光層之層中時,進一步較佳地,當化合物不含任何稠合芳基或雜芳基時,其中多於二個六員環係直接彼此稠合。尤佳地係Ar、R、R
1及R
2基團不含任何稠合芳基或雜芳基,其中二或更多個六員環係直接彼此稠合。對此,菲、聯伸三苯及喹唑啉形成了例外,由於彼等之高三重態能量,儘管存在稠合的芳族六員環卻可能係較佳的。
上述較佳實施例可在請求項1中所定義之限制內如所欲地彼此組合。在本發明之特佳實施例中,上述偏好同時發生。
本發明因此進一步提供一種用於製備本發明之化合物的方法,其特徵在於下列步驟:
(1)合成具有置換R*基團的反應性脫離基之式(1)化合物的基本骨架,該反應性脫離基較佳係選自硼酸、有機硼酸酯(boronic ester)、Cl、Br、I、三氟甲磺酸根(triflate)、甲苯磺酸根(tosylate)或甲磺酸根(mesylate);
(2)藉由偶合反應引入R*基團,尤其是當L係芳族或雜芳環系統時藉由Suzuki偶合,或者當L係單鍵時藉由Hartwig-Buchwald偶合。
為了從液相加工(例如藉由旋塗或藉由印刷方法)式(1)之化合物或較佳實施例之化合物,需要本發明之化合物的調配物。這些調配物可係例如溶液、分散液或乳液。為此,較佳可使用二或更多種溶劑之混合物。合適且較佳的溶劑係例如甲苯、苯甲醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、對稱三甲苯(mesitylene)、四氫萘、藜蘆醚、THF、甲基-THF、THP、氯苯、二㗁烷、苯氧基甲苯(尤其是3-苯氧基甲苯)、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯啶酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、異丙苯、環己醇、環己酮、環己基苯、十氫萘、十二烷基苯、苯甲酸乙酯、茚烷、NMP、對-異丙基甲苯、苯基乙基醚(phenetole)、1,4-二異丙基苯、二苄醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇單丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-異丙基萘、戊基苯、己基苯、庚基苯、辛基苯、1,1-雙(3,4-二甲基苯基)乙烷、2-甲基聯苯、3-甲基聯苯、1-甲基萘、1-乙基萘、辛酸乙酯、癸二酸二乙酯、辛酸辛酯、庚基苯、異戊酸薄荷酯(menthyl isovalerate)、己酸環己酯或這些溶劑之混合物。
本發明因此進一步提供一種調配物,其包含至少一種本發明之化合物及至少一種溶劑。
式(1)之化合物或上文詳述之較佳實施例之化合物根據本發明係用於電子裝置中,尤其是用於有機電致發光裝置中。本發明因此進一步提供本發明之化合物用於電子裝置中、尤其是用於有機電致發光裝置中的用途。
本發明進一步提供一種電子裝置,尤其是有機電致發光裝置,其包含至少一種式(1)之化合物或上文詳述之較佳實施例之化合物。
電子裝置在本發明的上下文中係一種包含至少一層的裝置,該層包含至少一種有機化合物。此組件亦可包含無機材料或亦完全由無機材料形成之層。
電子裝置較佳係選自由下列所組成之群組:有機電致發光裝置(OLED)、有機積體電路(O-IC)、有機場效電晶體(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)、染料敏化之有機太陽能電池(DSSC)、有機光學檢測器、有機感光器(photoreceptor)、有機場淬滅裝置(O-FQD)、發光電化學電池(LEC)、有機雷射二極體(O-雷射)及有機電漿子發射裝置(organic plasmon emitting device),但較佳係有機電致發光裝置(OLED),更佳係磷光OLED。
有機電致發光裝置包含陰極、陽極及至少一個發光層。除了此等層以外,有機電致發光裝置亦可包含其他層,例如在各情況下一或多個電洞注入層、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、電子阻擋層及/或電荷產生層。同樣可在二個發光層之間引入具有例如激子阻擋功能之中間層。然而,應指出的是,該等層中之每一者不一定必須存在。在此情況下,有機電致發光裝置可含有發光層,或其可含有複數個發光層。若存在複數個發光層,則這些發光層較佳地總體上具有在380 nm與750 nm之間的數個發射最大值,使得總體結果發白光;換言之,在發光層中使用可發螢光或發磷光之各種發光化合物。尤佳的是具有三個發光層的系統,其中該三個層顯示藍色、綠色及橙色或紅色發射。本發明之有機電致發光裝置亦可係串聯式OLED,尤其是用於發白光的OLED。
根據確切結構,根據上文詳述之實施例之化合物可用於不同的層中。較佳者係發光層中包含式(1)之化合物或上述較佳實施例之化合物作為磷光發射體或展現TADF(熱活化延遲螢光)的發射體(尤其是磷光發射體)的基質材料之有機電致發光裝置。在此情況下,有機電致發光裝置可含有發光層,或其可含有複數個發光層,其中至少一個發光層含有至少一種本發明之化合物作為基質材料。此外,本發明之化合物亦可用於電子傳輸層及/或電洞阻擋層及/或電洞傳輸層及/或激子阻擋層中。
當化合物用作發光層中的磷光化合物之基質材料時,較佳係與一或多種磷光材料(三重態發光體)組合使用。在本發明的上下文中,磷光係理解為意指來自具有較高自旋多重性(亦即自旋態> 1)之激發態、尤其是來自激發的三重態之發光。在本申請案的上下文中,所有具有過渡金屬或鑭系元素之發光錯合物(尤其是所有銥、鉑及銅錯合物)應視為磷光化合物。
式(1)之化合物或較佳實施例之化合物與發光化合物的混合物,以發射體及基質材料之總混合物計,含有在99體積%與1體積%之間、較佳地在98體積%與10體積%之間、更佳地在97體積%與60體積%之間、且尤其是在95體積%與80體積%之間的式(1)之化合物或較佳實施例之化合物。對應地,以發射體及基質材料之總混合物計,該混合物含有在1體積%與99體積%之間、較佳地在2體積%與90體積%之間、更佳地在3體積%與40體積%之間、且尤其是在5體積%與20體積%之間的發射體。
本發明之其他較佳實施例係式(1)之化合物或較佳實施例之化合物與其他基質材料組合作為磷光發射體之基質材料的用途。可與本發明之化合物組合使用之合適的基質材料係芳族酮、芳族氧化膦或芳族亞碸或碸(例如根據WO 2004/013080、WO 2004/093207、WO 2006/005627或WO 2010/006680)、三芳基胺、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、WO 2008/086851或WO 2013/041176中所揭示之咔唑衍生物)、吲哚并咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)、茚并咔唑衍生物(例如根據WO 2010/136109、WO 2011/000455、WO 2013/041176或WO 2013/056776)、氮雜咔唑衍生物(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(例如根據WO 2005/111172)、氮雜硼雜環戊二烯(azaborole)或有機硼酸酯(例如根據WO 2006/117052)、三衍生物(例如根據WO 2007/063754、WO 2008/056746、WO 2010/015306、WO 2011/057706、WO 2011/060859或WO 2011/060877)、鋅錯合物(例如根據EP 652273或WO 2009/062578)、二氮雜矽雜環戊二烯(diazasilole)或四氮雜矽雜環戊二烯衍生物(例如根據WO 2010/054729)、二氮雜磷雜環戊二烯(diazaphosphole)衍生物(例如根據WO 2010/054730)、橋聯咔唑衍生物(例如根據WO 2011/042107、WO 2011/060867、WO 2011/088877及WO 2012/143080)、聯伸三苯衍生物(例如根據WO 2012/048781)、或二苯并呋喃衍生物(例如根據WO 2015/169412、WO 2016/015810、WO 2016/023608、WO 2017/148564或WO 2017/148565)。同樣地其他比實際發射體短的波長發光之磷光發射體可作為共主體存在於混合物中,或者,如果有的話,不參與電荷傳輸至顯著程度的化合物,如例如WO 2010/108579中所述。
在本發明之較佳實施例中,該等材料係與其他基質材料組合使用。式(1)之化合物或較佳實施例之化合物係富電子化合物。較佳的共基質材料因此係較佳地選自三、嘧啶、喹唑啉、喹㗁啉及內醯胺、或這些結構之衍生物的群組之電子傳輸化合物。
可與本發明之化合物一起用作混合物之較佳的三、嘧啶、喹唑啉或喹㗁啉衍生物係下列式(7)、(8)、(9)及(10)之化合物:
其中R具有上文所給的含義。R較佳地在各情況下係相同或不同,且係H或芳族或雜芳族環系統,其具有6至30個芳族環原子且其可經一或多個R
1基團取代。
在本發明之較佳實施例中,式(7a)、(8a)、(9a)及(10a)中之Ar
1在各情況下係相同或不同,且係芳族或雜芳族環系統,其具有6至30個芳族環原子,尤其是6至24個芳族環原子,且可經一或多個R基團取代。合適的芳族或雜芳族環系統Ar
1在此與如上所述作為Ar
1之實施例者相同,尤其是結構Ar-1至Ar-83。
合適的磷光化合物(=三重態發射體)尤其是當經適當激發時發光(較佳地在可見光區域)且亦含有至少一個原子序大於20、較佳係大於38且小於84、更佳係大於56且小於80之原子,尤其是具有此原子序之金屬的化合物。所使用之較佳磷光發射體較佳係含有銅、鉬、鎢、錸、釕、鋨、銠、銥、鈀、鉑、銀、金或銪的化合物,尤其是含有銥或鉑的化合物。
上述發射體之實例可在下列申請案中找到:WO 00/70655、WO 2001/41512、WO 2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373、US 2005/0258742、WO 2009/146770、WO 2010/015307、WO 2010/031485、WO 2010/054731、WO 2010/054728、WO 2010/086089、WO 2010/099852、WO 2010/102709、WO 2011/032626、WO 2011/066898、WO 2011/157339、WO 2012/007086、WO 2014/008982、WO 2014/023377、WO 2014/094961、WO 2014/094960、WO 2015/036074、WO 2015/104045、WO 2015/117718、WO 2016/015815、WO 2016/124304、WO 2017/032439、WO 2018/011186及WO 2018/041769、WO 2019/020538、WO 2018/178001、WO 2019/115423及WO 2019/158453。一般而言,用於根據先前技術之磷光OLED以及如在有機電致發光領域中之所屬技術領域中具有通常知識者已知的所有磷光錯合物都是合適的,並且所屬技術領域中具有通常知識者在不鍛鍊發明技能的情況下將能夠使用其他磷光錯合物。
在本發明之有機電致發光裝置的其他層中,可使用根據先前技術一般所使用之任何材料。因此,所屬技術領域中具有通常知識者將能夠在不鍛鍊發明技能的情況下,與式(1)之化合物或上述較佳實施例之化合物組合使用對於有機電致發光裝置已知的任何材料。
額外較佳的是有機電致發光裝置,其特徵在於,藉由昇華方法來塗佈一或多層。在此情況下,在真空昇華系統中藉由氣相沉積在小於10
-5毫巴、較佳係小於10
-6毫巴之初始壓力下施加材料。然而,初始壓力亦可係甚至更低,例如低於10
-7毫巴。
同樣較佳者係有機電致發光裝置,其特徵在於,藉由OVPD(有機氣相沉積(organic vapour phase deposition))方法或借助於載體氣體昇華來塗佈一或多層。在此情況下,在10
-5毫巴與1巴之間的壓力下施加材料。此方法之特殊實例係OVJP(有機蒸氣噴射印刷)方法,其中直接藉由噴嘴來施加材料並因此將其結構化。
額外較佳者係有機電致發光裝置,其特徵在於從溶液中製造一或多層,例如藉由旋塗、或藉由任何印刷方法,例如網版印刷、柔版印刷、平版印刷、LITI(光誘導熱成像、熱轉移印刷)、噴墨印刷或噴嘴印刷。為此目的,需要可溶性化合物,其可例如透過適當取代而獲得。
此外,亦可係混雜方法,其中例如從溶液施加一或多層及藉由氣相沉積施加一或多個其他層。
這些方法係所屬技術領域中具有通常知識者一般已知的,並且可由所屬技術領域中具有通常知識者在不鍛鍊發明技能的情況下施加至包含式(1)之化合物的有機電致發光裝置。
值得注意的是本發明之材料及本發明之有機電致發光裝置比先前技術具有下列令人驚訝的優點中之一或多者:
1. 含有式(1)之化合物作為磷光發光體之基質材料的OLED得到長壽命。當化合物用作磷光發光體之基質材料時尤其如此。更具體地,相較於具有相同橋接聯伸三苯基本結構但具有不同取代模式且不完全是一個取代基R*之基質材料的OLED,OLED顯示出改進的壽命。
2. 含有式(1)之化合物的OLED得到高效率。當化合物用作磷光發光體之基質材料時尤其如此。
3. 含有式(1)之化合物的OLED得到低操作電壓。當化合物用作磷光發光體之基質材料時尤其如此。
藉由下列實例更詳細描述本發明,而非藉此意欲限制本發明。所屬技術領域中具有通常知識者將能夠使用所給資訊在所揭示之整個範疇內執行本發明,並且在不鍛鍊發明技能的情況下製造其他發明性電子裝置。
實例:
在惰性氣氛下,將容器初始地裝入DMSO(50 ml)、K
3PO
4(53.08 g, 250 mmol)、吡啶-2-羧酸(1.53 g, 12.44 mmol)及CuI(1.19 g, 6.22 mmol)。隨後,依次逐漸添加3-氯苯酚(19.20 g, 150 mmol)[108-43-0]及3-溴-1-氯苯(23.93 g, 125 mmol)[108-37-2],並將反應混合物在85°C下攪拌16小時。冷卻後,將反應混合物藉由用氨溶液及甲基三級丁基醚萃取來處理。將有機相用水洗滌五次並用飽和NaCl溶液洗滌兩次,將合併的相以Na
2SO
4乾燥,並在旋轉蒸發器上抽去溶劑。將粗製產物經由分餾進一步純化。產率:26.88 g(106 mmol),85%;純度;96%藉由
1H NMR。
可類似地製備下列化合物。不僅可藉由蒸餾還可使用管柱層析法、或使用其他標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷、二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶來進行純化。
將初始裝入的S1a(23.90 g, 100 mmol)之THF(150 ml)在惰性氣氛下冷卻至-75°C。隨後,以內部溫度不超過-65°C的方式逐漸地逐滴添加正丁基鋰(2.5 mol/l於己烷中,80 ml,200 mmol)。使混合物在-75°C下另外攪拌4小時,然後以內部溫度不超過-65°C的方式逐滴添加溴(5.6 ml, 109.3 mmol)。添加結束後,將混合物在-75°C下攪拌1小時,然後使其在1小時內逐漸溫熱至10°C,並在10°C下攪拌1小時。接著冷卻至0°C並用飽和Na
2SO
3溶液(50 ml)小心地淬熄混合物。將混合物藉由用甲苯及水萃取來處理,將合併的有機相用水洗滌三次及用飽和NaCl溶液洗滌一次並以Na
2SO
4乾燥,在旋轉蒸發器上移除溶劑。將粗製產物藉由在回流下與2-丙醇一起攪拌來萃取兩次。產率:24.21 g(86 mmol, 86%);純度:97%藉由
1H NMR。
可類似地製備下列化合物。不僅可藉由萃取性攪拌還可藉由蒸餾或管柱層析法、或使用其他標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷、二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶來進行純化。
將初始裝入的S1b(39.19 g, 140.0 mmol)、4-甲氧基苯基硼酸(22.79 g, 150.0 mmol)[5720-07-0]及K
2CO
3(38.70 g, 280.0 mmol)之THF(70 ml)及水(170 ml)惰性化30分鐘。隨後,添加肆(三苯基膦)鈀[14221-01-3](1.78 g, 1.54 mmol)並將反應混合物在回流下攪拌20小時。將混合物藉由用甲苯及水萃取來處理,將合併的有機相用水及用飽和NaCl溶液洗滌並以Na
2SO
4乾燥,在旋轉蒸發器上抽去溶劑。將粗製產物從乙醇中再結晶。產率:33.7 g(109 mmol, 78%),96%藉由
1H NMR。
可類似地製備下列化合物。可藉由管柱層析法、或使用其他標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷、二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶來進行純化。
將初始裝入的S1c(30.88 g, 100 mmol)及K
2CO
3(41.46 g, 300 mmol)在惰性氣氛下添加DMAc(450 ml),並將混合物惰性化30分鐘。隨後,添加Pd(OAc)
2(447 mg, 1.99 mmol)及氯化1,3-雙(2,6-二異丙基苯基)-3
H-咪唑-1-鎓(1.69 g, 3.98 mmol),並將反應混合物在150°C下攪拌16小時。冷卻後,將混合物倒入乙醇/水(1:1, 600 ml)中並另外攪拌30分鐘。將沉澱的固體抽吸濾出並用水洗滌五次及用乙醇洗滌3次。將粗製產物藉由在回流下與2-丙醇一起攪拌來萃取,並在冷卻後將固體抽吸濾出。產率:22.9 g(84 mmol, 84%),98%藉由
1H NMR。
可類似地製備下列化合物。在此不僅可使用氯化1,3-雙(2,6-二異丙基苯基)-3
H-咪唑-1-鎓還可使用三(三級丁基)膦或三環己基膦,或者作為Pd源不僅使用Pd(OAc)
2還有Pd
2(dba)
3。可藉由管柱層析法、或使用其他標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷、二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶來進行純化。
將初始裝入的S1d(27.23 g, 100 mmol)之二氯甲烷(620 ml)在冰浴中冷卻至0°C。隨後,小心地逐滴添加BBr
3(6.0 ml, 63.2 mmol)。在添加結束後,使混合物溫熱至室溫。轉化完成後,將混合物再次冷卻至0°C並小心地用MeOH(150 ml)淬熄。在旋轉蒸發器上抽去溶劑。隨後,向混合物中添加三次300 ml的MeOH,其各者係接著在旋轉蒸發器上移除。添加另一200 ml的MeOH,並將固體抽吸濾出。將粗製產物乾燥並用於下一階段而未進一步純化。
產率:17.05 g(66 mmol, 66%)。
可類似地製備下列化合物。可藉由管柱層析法、或使用其他標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷、二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶來進行純化。
將初始裝入的S1e(12.91 g, 50.0 mmol)及三乙胺(20.8 ml, 150 mmol)之二氯甲烷(700 ml)在冰浴中冷卻至0°C。隨後,緩慢逐滴添加三氟甲磺酸酐(10.9 ml, 65.0 mmol)。在添加結束後,使混合物溫熱至室溫。轉化完成後,將混合物用二氯甲烷及水進行萃取性處理,將合併的有機相以Na
2SO
4乾燥,並在旋轉蒸發器上移除溶劑。將殘餘物置於300 ml的環己烷中,並將混合物在室溫下攪拌30分鐘。將固體抽吸濾出並在真空乾燥箱中乾燥。產率13.74 g(35.2 mmol, 70%)。
可類似地製備下列化合物。可藉由管柱層析法、或使用其他標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷、二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶來進行純化。
將初始裝入的S9c(24.23 g, 100 mmol)之300 ml的THF冷卻至-75°C。隨後,以溫度不上升至-65°C以上的方式逐滴添加己基鋰(44.0 ml, c=2.5 mol/l, 110 mmol)。在添加結束後,將混合物在-75°C下攪拌1小時。隨後,使反應混合物逐漸溫熱至室溫並在室溫下攪拌1小時。隨後,將反應混合物冷卻回到-75°C,並以溫度不上升至-65°C以上的方式逐滴添加硼酸三甲酯(15.59 g, 150.0 mmol)。使混合物回到室溫整夜並在第二天用HCl(c=5 mol/l, 50 ml)小心地淬熄。將混合物藉由用水萃取來處理,並將有機相用水洗滌三次。藉由旋轉蒸發移除THF至50ml,然後添加150 ml的正庚烷,並將沉澱的固體抽吸濾出並用正庚烷洗滌。產率:24.03 g(84.2 mmol, 84%),96%藉由
1H NMR。
將初始裝入的S1f(11.71 g, 30.0 mmol)、雙()二硼(bis(pinacolato)diboron)(9.40 g, 36.3 mmol)及KOAc(8.90 g, 90.68 mmol)之1,4-二㗁烷(200 ml)用氬氣惰性化30分鐘。隨後,添加Pd(dppf)Cl
2(740 mg, 0.91 mmol),並將混合物在回流下攪拌20小時。冷卻後,在旋轉蒸發器上移除溶劑,並將殘餘物藉由用二氯甲烷及水萃取來處理。將合併的有機相以Na
2SO
4乾燥,添加乙醇(150 ml),並在旋轉蒸發器上抽去二氯甲烷。將沉澱的固體抽吸濾出並在真空乾燥箱中乾燥。將粗製產物用於下一階段而未進一步純化。產率:9.06 g(24.6 mmol, 82%),純度95%藉由
1H NMR。
可類似地製備下列化合物。作為替代方案,所使用的催化劑系統可係Pd(PCy
3)
2Cl
2或Pd
2(dba)
3與S-Phos(1:3)。不僅可藉由管柱層析法還可藉由熱萃取、或使用其他標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷)再結晶或熱萃取、或使用高沸點物質(諸如二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶或熱萃取來進行純化。
將初始裝入的S9e(27.28 g, 100 mmol)及K
3PO
4(42.7 g, 200 mmol)之DMAc(1000 ml)在惰性氣氛下在140°C攪拌16小時。冷卻後,在旋轉蒸發器上大量地抽去DMAc,並將殘餘物藉由用二氯甲烷及水萃取來處理。將粗製產物經由管柱層析法純化。產率:18.33 g(71.1 mmol; 71%)。
本發明化合物之製備
將初始裝入的S1f(19.13 g, 49.0 mmol)、9-苯基-9H,9’H-[3,3’]雙咔唑(22.04 g, 53.9 mmol)[1060735-14-9]及LiOtBu(8.76 g, 108.3 mmol)之鄰二甲苯(1000 ml)用氬氣惰性化30分鐘。隨後,依次添加Pd(OAc)
2(221 mg, 1.0 mmol)及S-Phos(815 mg, 2.0 mmol),並將反應混合物加熱至回流18小時。將混合物藉由用甲苯/水萃取來處理。將合併的有機相以Na
2SO
4乾燥,並在旋轉蒸發器上抽去溶劑。將粗製產物用甲苯在氧化鋁上進行鹼性熱萃取四次,然後從DMAc中再結晶兩次,最後在高真空下昇華。產率:13.63 g(21.0 mmol; 43%)。
可類似地製備下列化合物。所使用的催化劑系統不僅可係具有Pd(OAc)
2或Pd
2(dba)
3的S-Phos還可係具有 Pd(OAc)
2或Pd
2(dba)
3的X-Phos作為鈀源。所使用的溶劑不僅可係鄰二甲苯,尤其還可係甲苯。可使用管柱層析法、熱萃取或再結晶進行純化。可使用標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷)再結晶或熱萃取、或使用高沸點物質(諸如二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶或熱萃取。
將初始裝入的S3f(15.61 g, 40.0 mmol)、(B-[3-(9’-苯基[3,3’-聯-9H-咔唑]-9-基)苯基]硼酸(22.72 g, 43.0 mmol)[CAS-1398394-64-3]及K
3PO
4(15.54 g, 73.2 mmol)之THF(400 ml)及水(100 ml)用氬氣除氣30分鐘。隨後,依次添加Pd(OAc)
2(204 mg, 0.91 mmol)及X-Phos(905 mg, 1.82 mmol),並將混合物在回流下攪拌30小時。將沉澱的固體抽吸濾出,用水及THF洗滌兩次,然後用乙醇洗滌。將粗製產物用甲苯在氧化鋁上進行鹼性熱萃取五次,且最後在高真空下昇華。產率:15.95 g(22.0 mmol, 55%);純度:> 99.9%藉由HPLC。
可類似地製備下列化合物。所使用的催化劑系統亦可係S-Phos或P(o-tol)
3與Pd
2(dba)
3或Pd(OAc)
2。可使用管柱層析法、熱萃取或再結晶進行純化。可使用標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷)再結晶或熱萃取、或使用高沸點物質(諸如二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶或熱萃取。
將初始裝入的S1g(28.61 g, 100 mmol)、雙(聯苯-4-基)(4-溴苯基)胺(47.64 g, 100 mmol)及K
3PO
4(63.79 g, 300 mmol)之THF(1200 ml)及水(300 ml)用氬氣惰性化30分鐘。隨後,依次添加Pd(OAc)
2(448 mg, 2.00 mmol)及X-Phos(1.99 g, 4.00 mmol),並將混合物在回流下攪拌16小時。冷卻後,將沉澱的固體抽吸濾出並用水及乙醇洗滌。將粗製產物用鄰二甲苯在氧化鋁上進行鹼性熱萃取四次,且最後在高真空下昇華。
產率:54.58 g(62.3 mmol, 62%);純度:> 99.9%藉由HPLC。
可類似地製備下列化合物。所使用的催化劑系統不僅可係X-Phos,還可係S-Phos,其不僅具有Pd(OAc)
2,還具有Pd
2(dba)
3、或Pd(PPh
3)
2Cl
2或Pd(PPh
3)
4。所使用的溶劑不僅可係鄰二甲苯,尤其還可係甲苯。可使用管柱層析法、熱萃取或再結晶進行純化。可使用標準溶劑(諸如乙醇、丁醇、丙酮、乙酸乙酯、乙腈、甲苯、二甲苯、二氯甲烷、甲醇、四氫呋喃、乙酸正丁酯、1,4-二㗁烷)再結晶或熱萃取、或使用高沸點物質(諸如二甲亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等)進行再結晶或熱萃取。
OLED的製造
下列實施例(請參見表1至3)藉由與先前技術的材料進行比較,呈現出本發明之化合物在OLED中的用途。
實例V1至V8及E1a至E8c之預處理:
在塗佈之前,將塗佈有厚度為50 nm之結構化ITO(銦錫氧化物)的玻璃板進行處理,先用氧電漿、接著用氬電漿。此等經電漿處理的玻璃板形成將OLED施加於其上的基板。
基本上OLED具有下列層結構:基板/電洞注入層(HIL)/電洞傳輸層(HTL)/電子阻擋層(EBL)/發光層(EML)/可選的電洞阻擋層(HBL)/電子傳輸層(ETL)/可選的電子注入層(EIL)及最後係陰極。藉由厚度為100 nm之鋁層來形成陰極。OLED之確切結構可在表1中找到。生產OLED所需的材料(若之前尚未描述過)顯示於表3中。表2中列出OLED之裝置數據。實例V1至V8係比較例。實例E1a-f、E2a-e、E3a、E3b、E4a-c、E5a-e、E6a、E7a、E7b及E8a-c顯示本發明之OLED的數據。
藉由在真空腔室內進行熱氣相沉積來施加所有材料。在此情況下,發光層總是由至少二種基質材料及發光摻雜劑(發射體)組成,該發光摻雜劑係藉由共蒸發以特定的體積比添加至基質材料中。以E1:P1a:TE2(32%: 60%:8%)的形式給出的細節在此意指材料E1以32體積%的比例、P1a以60體積%的比例及TE2以8體積%的比例存在於層中。類似地,電子傳輸層亦可由二種材料之混合物所組成。
在1000 cd/m²的亮度下判定電致發光光譜,並由此計算CIE 1931 x及y色坐標。表9中之參數U10係指電流密度為10 mA/cm²所需的電壓。EQE10表示在10 mA/cm²下達到的外部量子效率。壽命LT係定義為在恆定電流密度j
0的操作過程中,在正向所測量之亮度(以cd/m²計)從起始亮度降至一定比例L1之後的時間。表9中L1=80%之數字意指LT欄中所記述的壽命對應於亮度(以cd/m²計)下降至其起始值的80%之後的時間。
本發明之化合物在OLED中的用途
Claims (14)
- 一種式(1)之化合物, 其中R基團亦可能出現多於一次且所使用的符號係: Z 係O或S; R* 係式(2)或(3)之基團,其中虛線鍵表示至式(1)之基本骨架的鍵, X 在各情況下係相同或不同,且係CR或N,其中不多於二個X基團係N,或二個相鄰X基團係下列式(4)或(5)之基團: 其中虛線鍵表示式(2)中該基團之鍵聯; Y 在各情況下係相同或不同,且係CR或N; W 在各情況下係相同或不同,且係NAr 2、O、S或C(R) 2; L 係單鍵或芳族或雜芳族環系統,其具有5至24個芳族環原子且可經一或多個R基團取代; A 1、Ar 2在各情況下係相同或不同,且係芳族或雜芳族環系統,其具有5至40個芳族環原子且可經一或多個R基團取代; R 在各情況下係相同或不同,且係H;D;F;Cl;Br;I;CN;NO 2;OR 1;SR 1;COOR 1;C(=O)N(R 1) 2;Si(R 1) 3;B(OR 1) 2;C(=O)R 1;P(=O)(R 1) 2;S(=O)R 1;S(=O) 2R 1;OSO 2R 1;具有1至20個碳原子之直鏈烷基或具有2至20個碳原子之烯基或炔基或具有3至20個碳原子之支鏈或環狀烷基,其中該烷基、烯基或炔基在各情況下可經一或多個R 1基團取代,其中一或多個非相鄰CH 2基團可經Si(R 1) 2、C=O、NR 1、O、S或CONR 1置換;或芳族或雜芳族環系統,其具有5至60個芳族環原子、較佳係5至40個芳族環原子,且在各情況下可經一或多個R 1基團取代;同時,二個R基團一起亦可形成脂族、雜脂族、芳族或雜芳族環系統; R 1在各情況下係相同或不同,且係H;D;F;Cl;Br;I;CN;NO 2;OR 2;SR 2;Si(R 2) 3;B(OR 2) 2;C(=O)R 2;P(=O)(R 2) 2;S(=O)R 2;S(=O) 2R 2;OSO 2R 2;具有1至20個碳原子之直鏈烷基或具有2至20個碳原子之烯基或炔基或具有3至20個碳原子之支鏈或環狀烷基,其中該烷基、烯基或炔基可各自經一或多個R 2基團取代,其中一或多個非相鄰CH 2基團可經Si(R 2) 2、C=O、NR 2、O、S或CONR 2置換,且其中在該烷基、烯基或炔基中之一或多個氫原子可經D、F、Cl、Br、I或CN置換;或芳族或雜芳族環系統,其具有5至40個芳族環原子,且在各情況下可經一或多個R 2基團取代;同時,二或更多個R 1基團一起亦可形成脂族環系統; R 2在各情況下係相同或不同,且係H、D、F、CN或具有1至20個碳原子之脂族、芳族或雜芳族有機基團,尤其係烴基基團,其中一或多個氫原子亦可經F置換。
- 如請求項1至3中一或多項之化合物,其中該化合物含有不多於二個取代基R,該取代基R是H或D以外的基團。
- 如請求項1至5中一或多項之化合物,其中L係選自單鍵及鄰-、間-或對-鍵結的伸苯基。
- 如請求項1至6中一或多項之化合物,其中,在式(2)中,所有X基團在各情況下均相同或不同且係CR,或者二個相鄰X係式(4)之基團,其中式(4)中之Y在各情況下係相同或不同且係CR,而其他二個X在各情況下係相同或不同且係CR。
- 一種用於製備如請求項1至8中一或多項之化合物的方法,其特徵在於下列步驟: (1) 合成含有置換R*基團的反應性脫離基之式(1)化合物的基本骨架; (2) 藉由偶合反應引入R*基團。
- 一種調配物,其包含至少一種如請求項1至8中之一或多項之化合物及至少一種溶劑。
- 一種如請求項1至8中之一或多項之化合物於電子裝置中之用途。
- 一種電子裝置,其包含至少一種如請求項1至8中之一或多項之化合物。
- 如請求項12之電子裝置,其係有機電致發光裝置,其中,將如請求項1至8中之一或多項之化合物與至少一種磷光發射體組合用於發光層中。
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