TWI702276B - 新穎化合物以及包括此化合物的有機發光裝置 - Google Patents
新穎化合物以及包括此化合物的有機發光裝置 Download PDFInfo
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- TWI702276B TWI702276B TW108115252A TW108115252A TWI702276B TW I702276 B TWI702276 B TW I702276B TW 108115252 A TW108115252 A TW 108115252A TW 108115252 A TW108115252 A TW 108115252A TW I702276 B TWI702276 B TW I702276B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 92
- 239000000126 substance Substances 0.000 claims abstract description 36
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 9
- 229910052786 argon Inorganic materials 0.000 claims description 7
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- 239000004305 biphenyl Substances 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical class [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Images
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
-
- 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- 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
- C07C13/72—Spiro hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
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Abstract
本發明提供一種由化學式1表示的新穎化合物以及一種
包括此化合物的有機發光裝置。在化學式1中,各取代基的定義與實施方式中所定義的相同。
Description
[相關申請案的交叉參考]
本申請案主張於2018年5月3日向韓國智慧財產局(Korean Intellectual Property Office)申請的韓國專利申請案第10-2018-0051361號的申請日權益,所述專利申請案的全部內容以引用的方式併入本文中。
本發明是關於一種新穎化合物且是關於一種包括此化合物的有機發光裝置。
一般而言,有機發光現象是指藉由使用有機材料將電能轉換成光能的現象。使用有機發光現象的有機發光裝置具有諸如寬視角、極佳對比度、快速回應時間、極佳亮度、驅動電壓以及回應速度的特徵,且由此進行了許多研究。
有機發光裝置一般具有包括陽極、陰極以及插入於陽極與陰極之間的有機材料層的結構。有機材料層常常具有包括不同材料的多層結構,以便增強有機發光裝置的效率及穩定性,且例如有機材料層可由電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層以及類似者形成。在有機發光裝置的結構中,若電壓施
加於兩個電極之間,則電洞自陽極注入至有機材料層中且電子自陰極注入至有機材料層中,且在所注入的電洞及電子彼此相遇時形成激子(exciton),且在激子再次降低至基態時發光。
繼續需要針對用於這些有機發光裝置的有機材料研發新材料。
[先前技術文獻]
[專利文獻]
(專利文獻0001)韓國專利特許公開案第10-2000-0051826號
本發明的目標是提供一種新穎化合物以及一種包含此化合物的有機發光裝置。
在化學式1中,L為單鍵;經取代或未經取代的C6-60伸芳基;或含有由N、O以及S所構成的族群中選出的至少一者的經取代或未經取代的
C2-60伸雜芳基,且Ar為含有由N、O以及S所構成的族群中選出的至少一者的經取代或未經取代的C2-60雜芳基。
在本發明的另一態樣中,提供有一種有機發光裝置,包含:第一電極;與第一電極相對設置的第二電極;以及設置於第一電極與第二電極之間的一或多個有機材料層,其中有機材料層中的一或多個層包含由化學式1表示的化合物。
上述由化學式1表示的化合物可用作有機發光裝置的有機材料層的材料,且可提高效率,實現低驅動電壓及/或改良有機發光裝置中的使用壽命特徵。特定言之,上述由化學式1表示的化合物可用作電洞注入、電洞傳輸、電洞注入及傳輸、發光、電子傳輸或電子注入的材料。
1:基底
2:陽極
3:有機材料層
4:陰極
5:電洞注入層
6:電洞傳輸層
7:電子阻擋層
8:發光層
9:電洞阻擋層
10:電子傳輸層
11:電子注入層
圖1繪示有機發光裝置的實例,所述有機發光裝置包括基底1、陽極2、有機材料層3以及陰極4。
圖2繪示有機發光裝置的實例,所述有機發光裝置包括基底1、陽極2、電洞注入層5、電洞傳輸層6、電子阻擋層7、發光層8、電洞阻擋層9、電子傳輸層10、電子注入層11以及陰極4。
在下文中,將更詳細地描述本發明以促進對本發明之理
解。
在本發明的一個實施例中,提供一種由化學式1表示的化合物。
如本文中所使用,術語「經取代或未經取代」意指未經取代或經由下列所構成的族群中選出的一或多個取代基取代:氘;鹵基;腈基;硝基;羥基;羰基;酯基;醯亞胺基;胺基;氧化膦基;烷氧基;芳氧基;烷基硫醇基;芳基硫醇基;烷基硫氧基;芳基硫氧基;矽烷基;硼基;烷基;環烷基;烯基;芳基;芳烷基;芳烯基;烷芳基;烷胺基;芳烷基胺基;雜芳基胺基;芳胺基;芳膦基;以及含有N、O以及S原子中的至少一者或未經取代或經取代基取代的雜環基,所述取代基與以上所例示的取代基中的兩個或多於兩個取代基鍵聯。舉例而言,「與兩個或多於兩個取代基鍵聯的取代基」可為聯苯基。亦即,聯苯基亦可為芳基,且可解釋為與兩個苯基鍵聯的取代基。
在本說明書中,羰基的碳原子數目不受特定限制,但較佳為1至40。具體言之,羰基可為具有以下結構式的化合物,但不限於此。
在本說明書中,對於酯基而言,酯基中的氧可經具有1個至25個碳原子的直鏈、分支鏈或環狀烷基或具有6個至25個碳原子的芳基取代。具體言之,酯基可為具有以下結構式的化合物,但不限於此。
在本發明中,醯亞胺基的碳原子數目不受特定限制,但較佳為1至25。具體言之,醯亞胺基可為具有以下結構式的化合物,但不限於此。
在本說明書中,矽烷基具體地包含三甲基矽烷基、三乙基矽烷基、第三丁基二甲基矽烷基、乙烯基二甲基矽烷基、丙基二甲基矽烷基、三苯基矽烷基、二苯基矽烷基、苯基矽烷基以及類似基團,但不限於此。
在本說明書中,硼基具體地包含三甲基硼基(trimethylboron group)、三乙基硼基(triethylboron group)、第三丁基二甲基硼基(t-butyldimethylboron group)、三苯基硼基(triphenylboron group)以及苯基硼基(phenylboron group),但不限於此。
在本說明書中,鹵基的實例包含氟、氯、溴或碘。
在本說明書中,烷基可為直鏈或分支鏈,且其碳原子數目不受特定限制,但較佳為1至40。根據一個實施例,烷基的碳原子數目為1至20。根據另一實施例,烷基的碳原子數目為1至10。根據另一實施例,烷基的碳原子數為1至6。烷基的具體實例包含甲基、乙基、丙基、正丙基、異丙基、丁基、正丁基、異丁基、第三丁基、第二丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、異戊基、新戊基、第三戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、環戊基甲基、環己基甲基、辛基、正辛基、第三辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、異己基、2-甲基戊基、4-甲基己基、5-甲基己基以及類似基團,但不限於此。
在本說明書中,烯基可為直鏈或分支鏈,且其碳原子數目不受特定限制,但較佳為2至40。根據一個實施例,烯基的碳原子數目為2至20。根據另一實施例,烯基的碳原子數目為2至10。根據又另一實施例,烯基的碳原子數目為2至6。烯基的具體實例包含乙烯基、1-丙烯基、異丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-雙(二苯基-1-基)乙烯基-1-基、芪基(stilbenyl group)、苯乙烯基(styrenyl group)以及類似基團,但不限於此。
在本說明書中,環烷基不受特定限制,但其碳原子數目較
佳為3至60。根據一個實施例,環烷基的碳原子數目為3至30。根據另一實施例,環烷基的碳原子數目為3至20。根據又另一實施例,環烷基的碳原子數目為3至6。環烷基的具體實例包含環丙基、環丁基、環戊基、3-甲基環戊基、2,3-二甲基環戊基、環己基、3-甲基環己基、4-甲基環己基、2,3-二甲基環己基、3,4,5-三甲環已基、4-第三丁基環己基、環庚基、環辛基以及類似基團,但不限於此。
在本發明書中,芳基不受特定限制,但較佳具有6個至60個碳原子,且可為單環芳基或多環芳基。根據一個實施例,芳基的碳原子數目為6至30。根據一個實施例,芳基的碳原子數目為6至20。芳基可為苯基、聯苯基、聯三苯基或如單環芳基的類似基團,但不限於此。多環芳基的實例包含萘基(naphthyl group)、蒽基(anthracenyl group)、菲基(phenanthryl)、芘基(pyrenyl group)、苝基(perylenyl group)、屈基(chrysenyl group)以及芴基(fluorenyl group)或類似基團,但不限於此。
在本說明書中,雜環基為包含O、N、Si以及S中的一或多者作為雜原子的雜環基,且其碳原子數目不受特定限制,但較佳
為2至60。雜環基的實例包含噻吩基(thiophene group)、呋喃基(furan group)、吡咯基(pyrrole group)、咪唑基(imidazole group)、噻唑基(thiazole group)、噁唑基(oxazole group)、噁二唑基(oxadiazol group)、三唑基(triazol group)、吡啶基(pyridyl group)、二吡啶基(bipyridyl group)、嘧啶基(pyrimidyl group)、三嗪基(triazine group)、吖啶基(acridyl group)、噠嗪基(pyridazine group)、吡嗪基(pyrazinyl group)、喹啉基(quinolinyl group)、喹唑啉基(quinazoline group)、喹喏啉基(quinoxalinyl group)、酞嗪基(phthalazinyl group)、吡啶并嘧啶基(pyridopyrimidinyl group)、吡啶并吡嗪基(pyridopyrazinyl group)、吡嗪并吡嗪基(pyrazinopyrazinyl group)、異喹啉基(isoquinoline group)、吲哚基(indole group)、咔唑基(carbazole group)、苯并噁唑基(benzoxazole group)、苯并咪唑基(benzimidazole group)、苯并噻唑基(benzothiazole group)、苯并咔唑基(benzocarbazole group)、苯并噻吩基(benzothiophene group)、二苯并噻吩基(dibenzothiophene group)、苯并呋喃基(benzofuranyl group)、啡啉基(phenanthroline group)、異噁唑基(isoxazolyl group)、噻二唑基(thiadiazolyl group)、啡噻嗪基(phenothiazinyl group)、二苯并呋喃基(dibenzofuranyl group)以及類似基團,但不限於此。
在本說明書中,芳烷基、芳烯基、烷芳基以及芳胺基中的芳基與芳基的前述實例相同。在本說明書中,芳烷基、烷芳基以及烷胺基中的烷基與烷基的前述實例相同。在本說明書中,雜芳基胺基中的雜芳基可應用於雜環基的前述描述。在本發明書中,芳烯基中的烯基與烯基的前述實例相同。在本說明書中,可應用除二價伸
芳基以外的芳基的前述描述。在本說明書中,可應用除二價伸雜芳基以外的雜環基的前述描述。在本說明書中,可應用除非單價烴環以外但藉由組合兩個取代基形成的芳基或環烷基的前述描述。在本說明書中,可應用除非單價雜環基以外但藉由組合兩個取代基形成的雜環基的前述描述。
其中,X1至X3為N或CH,其限制條件為X1至X3中的至少一者為N,Ar1及Ar2各自獨立地為經取代或未經取代的C6-60芳基;或含有由N、O以及S所構成的族群中選出的至少一者的經取代或未經取代的C2-60雜芳基,X4及X5為N或CH,其限制條件為X4及X5中的至少一者為N,每一Ar3獨立地為經取代或未經取代的C6-60芳基;或含有由N、O以及S所構成的族群中選出的至少一者的經取代或未經取代
的C2-60雜芳基,Y為N(Ar5)、O或S,Ar4為氫、經取代或未經取代的C6-60芳基或含有由N、O以及S所構成的族群中選出的至少一者的經取代或未經取代的C2-60雜芳基,且Ar5為經取代或未經取代的C6-60芳基。
較佳地,Ar1及Ar2各自獨立地為苯基、聯苯基、聯三苯基、萘基、菲基、聯伸三苯基、二苯并呋喃基、二苯并噻吩基或9-苯基-9H-咔唑基。
較佳地,Ar3為苯基、聯苯基或萘基。
較佳地,Ar4為氫、苯基、聯苯基或萘基。
較佳地,Ar5為苯基。
在本發明的另一實施例中,提供一種用於製備由化學式1表示的化合物的方法,如以下反應方案1或反應方案2中所繪示。
在反應方案1及反應方案2中,L及Ar與如以上所定義
的L及Ar相同,X'為鹵素,較佳地為溴或氯。反應方案1及反應方案2為鈴木偶合反應(Suzuki coupling reaction),所述鈴木偶合反應較佳地在鈀催化劑及鹼存在的情況下實施,且鈴木偶合反應的反應性基團可如所屬技術領域中所已知經修改。可在稍後將描述的製備實例中進一步說明以上製備方法。
在本發明的又另一實施例中,提供一種有機發光裝置,其包含由化學式1表示的化合物。作為實例,提供一種有機發光裝置,包含:第一電極;與第一電極相對設置的第二電極;以及設置於第一電極與第二電極之間的一或多個有機材料層,其中有機材料層中的一或多個層包含由化學式1表示的化合物。
本發明的有機發光裝置的有機材料層可具有單層結構,或其可具有多層結構,所述多層結構中堆疊了兩個或多於兩個有機材料層。舉例而言,本揭露的有機發光裝置可具有包括電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層以及類似者作為有機材料層的結構。然而,有機發光裝置的結構不限於此,且其可包含更少數目的有機層。
另外,有機材料層可包含發光層,其中發光層包含由化學式1表示的化合物。特定言之,根據本發明的化合物可用作發光層中的摻雜劑。
另外,有機材料層可包含電子傳輸層或電子注入層,其中電子傳輸層或電子注入層包含由化學式1表示的化合物。
另外,電子傳輸層、電子注入層或同時執行電子傳輸以及電子注入的層包含由化學式1表示的化合物。
另外,有機材料層包含發光層及電子傳輸層,其中電子傳
輸層可包含由化學式1表示的化合物。
另外,根據本發明的有機發光裝置可為正常型(normal type)有機發光裝置,在所述正常型有機發光裝置中將陽極、一或多個有機材料層以及陰極依序堆疊在基底上。另外,根據本揭露的有機發光裝置可為倒置型(inverted type)有機發光裝置,在所述倒置型有機發光裝置中將陰極、一或多個有機材料層以及陽極依序堆疊在基底上。舉例而言,根據本揭露的實施例的有機發光裝置的結構在圖1及圖2中示出。
圖1繪示有機發光裝置的實例,所述有機發光裝置包括基底1、陽極2、有機材料層3以及陰極4。在此結構中,由化學式1表示的化合物可包含於有機材料層中。
圖2繪示有機發光裝置的實例,所述有機發光裝置包括基底1、陽極2、電洞注入層5、電洞傳輸層6、電子阻擋層7、發光層8、電洞阻擋層9、電子傳輸層10、電子注入層11以及陰極4。在此結構中,由化學式1表示的化合物可包含於電洞注入層、電洞傳輸層、電子阻擋層、發光層、電洞阻擋層、電子傳輸層以及電子注入層中的一或多個層中。
除了有機材料層中的一或多個層包含由化學式1表示的化合物以外,根據本發明的有機發光裝置可由所屬技術領域中已知的材料及方法製造。另外,在有機發光裝置包含多個有機材料層時,有機材料層可由相同材料或不同材料形成。
舉例而言,根據本發明的有機發光裝置可藉由將第一電極、有機材料層以及第二電極依序堆疊在基底上來製造。在此情況下,有機發光裝置可藉由以下製造:使用諸如濺鍍(sputtering)法
或電子束蒸發(e-beam evaporation)法的物理氣相沈積(physical vapor deposition;PVD)方法將金屬、具有導電性的金屬氧化物或其合金沈積在基底上以形成陽極;將包含電洞注入層、電洞傳輸層、發光層以及電子傳輸層的有機材料層形成於所述陽極上;以及隨後將可用作陰極的材料沈積於所述有機材料層上。除此方法之外,有機發光裝置可藉由將陰極材料、有機材料層以及陽極材料依序沈積在基底上來製造。
另外,由化學式1表示的化合物可在製造有機發光裝置時藉由溶液塗佈法以及真空沈積法形成為有機層。在本文中,溶液塗佈法意指旋塗、浸塗、刀片刮抹、噴墨印刷、網版印刷、噴塗法、滾塗法或類似方法,但不限於此。
除此方法之外,有機發光裝置可藉由將陰極材料、有機材料層以及陽極材料依序沈積在基底上來製造(國際公開案WO2003/012890)。然而,製造方法不限於此。
作為實例,第一電極為陽極且第二電極為陰極,或替代地第一電極為陰極且第二電極為陽極。
作為陽極材料,一般而言,較佳地使用具有較大功函數的材料,以使得可將電洞平穩地注入至有機材料層中。陽極材料的具體實例包含:金屬,諸如釩、鉻、銅、鋅以及金,或其合金;金屬氧化物,諸如氧化鋅(zinc oxides)、氧化銦(indium oxides)、氧化銦錫(indium tin oxides;ITO)以及氧化銦鋅(indium zinc oxides;IZO);金屬與氧化物的組合,諸如ZnO:Al或SNO2:Sb;導電聚合物,諸如聚(3-甲基噻吩)(poly(3-methylthiophene))、聚[3,4-(伸乙基-1,2-二氧基)噻吩](poly[3,4-(ethylene-1,2-dioxy)thiophene];
PEDOT)、聚吡咯(polypyrrole)以及聚苯胺(polyaniline)以及類似材料,但不限於此。
作為陰極材料,一般而言,較佳地使用具有較小功函數的材料,以使得可容易地將電子注入至有機材料層中。陰極材料的具體實例包含:金屬,諸如鎂、鈣、鈉、鉀、鈦、銦、釔、鋰、釓、鋁、銀、錫以及鉛,或其合金;多層結構材料,諸如LiF/Al或LiO2/Al,以及類似材料,但不限於此。
電洞注入層為自電極注入電洞的層,且電洞注入材料較佳為一種化合物,所述化合物具有傳輸電洞的能力,由此在陽極中具有電洞注入效應且對於發光層或發光材料具有極佳電洞注入效應,防止發光層中所產生的激子移動至電子注入層或電子注入材料,且形成薄膜的能力為極佳的。較佳地,電洞注入材料的最高佔用分子軌域(highest occupied molecular orbital;HOMO)在陽極材料的功函數與周邊有機材料層的HOMO之間。電洞注入材料的具體實例包含金屬卟啉(metal porphyrine)、寡聚噻吩(oligothiophene)、芳胺(arylamine)類有機材料、己腈六氮雜苯并菲(hexanitrilehexaazatriphenylene)類有機材料、喹吖啶酮(quinacridone)類有機材料、苝(perylene)類有機材料、蒽醌(anthraquinone)、聚苯胺、聚噻吩(polythiophene)類導電聚合物以及類似材料,但不限於此。
電洞傳輸層為自電洞注入層接收電洞且將電洞傳輸至發光層的層。電洞傳輸材料適合地為具有較大電洞遷移率的材料,所述電洞傳輸材料可自陽極或電洞注入層接收電洞且將電洞轉移至發光層。所述電洞傳輸材料的具體實例包含芳胺類有機材料、導電
聚合物、同時存在共軛部分及非共軛部分的嵌段共聚物以及類似材料,但不限於此。
發光材料較佳為可接收分別自電洞傳輸層及電子傳輸層傳輸的電洞及電子且使電洞與電子組合以在可見光區域內發光的材料,且所述發光材料對螢光或磷光具有良好量子效率。發光材料的具體實例包含:8-羥基-喹啉鋁錯合物(Alq3);咔唑類化合物;二聚苯乙烯基(dimerized styryl)化合物;BAlq;10-羥基苯并喹啉-金屬化合物;苯并噁唑、苯并噻唑以及苯并咪唑類化合物;聚(對伸苯基伸乙烯基(poly(p-phenylenevinylene);PPV)類聚合物;螺環(spiro)化合物;聚芴、紅螢烯(lubrene)以及類似材料,但不限於此。
發光層可包含主體材料及摻雜劑材料。主體材料可為稠合芳族環衍生物、含雜環的化合物或類似材料。稠合芳族環衍生物的具體實例包含蒽衍生物、芘衍生物、萘衍生物、稠五苯(pentacene)衍生物、菲化合物、丙二烯合芴(fluoranthene)化合物以及類似衍生物。含雜環化合物的實例包含咔唑衍生物、二苯并呋喃衍生物、梯型(ladder-type)呋喃化合物、嘧啶衍生物以及類似化合物,但不限於此。
摻雜劑材料的實例包含芳族胺衍生物、苯乙烯基胺化合物、硼錯合物、丙二烯合芴化合物、金屬錯合物以及類似材料。具體言之,芳族胺衍生物為具有芳胺基的經取代或未經取代的稠合芳族環衍生物,且其實例包含具有芳胺基的芘、蒽、屈、二茚并芘以及類似衍生物。苯乙烯基胺化合物為至少一個芳基乙烯基在經取代或未經取代的芳胺中經取代的化合物,其中一或兩個或大於
兩個取代基經取代或未經取代,所述取代基是由下列所構成的族群中選出:芳基、矽烷基、烷基、環烷基以及芳胺基。所述苯乙烯基胺化合物的具體實例包含苯乙烯基胺、苯乙烯基二胺、苯乙烯基三胺、苯乙烯基四胺以及類似物,但不限於此。另外,金屬錯合物包含銥錯合物、鉑錯合物以及類似錯合物,但不限於此。
電子傳輸層為自電子注入層接收電子且將電子傳輸至發光層的層,且電子傳輸材料宜為可很好地自陰極接收電子且將電子轉移至發光層的材料,且對電子具有較大遷移率。電子傳輸材料的具體實例包含:8-羥基喹啉的Al錯合物;包含Alq3的錯合物;有機基團化合物;羥基黃酮-金屬錯合物以及類似材料,但不限於此。如根據先前技術所使用,電子傳輸層可與任何所需陰極材料一起使用。特定言之,陰極材料的適當實例為具有低功函數的典型材料,隨後為鋁層或銀層。所述陰極材料的特定實例包含銫、鋇、鈣、鐿以及釤,在每一情況下,隨後為鋁層或銀層。
電子注入層為自電極注入電子的層,且較佳為如下化合物:具有傳輸電子的能力,具有自陰極注入電子的效應及將電子注入至發光層或發光材料中的極佳效應,防止由發光層產生的激子移動至電洞注入層,且形成薄膜的能力亦為極佳的。電子注入層的具體實例包含芴酮(fluorenone)、蒽醌二甲烷(anthraquinodimethane)、聯苯醌(diphenoquinone)、硫代哌喃二氧化物(thiopyran dioxide)、噁唑、噁二唑、三唑、咪唑、苝四羧酸(perylenetetracarboxylic acid)、亞芴基甲烷(fluorenylidene methane)、蒽酮(anthrone)以及類似者,及其衍生物,金屬錯合物化合物、含氮的5員環衍生物,以及類似者,但不限於此。
金屬錯合物化合物的實例包含8-羥基喹啉根基(hydroxyquinolinato)鋰、雙(8-羥基喹啉根基)鋅、雙(8-羥基喹啉根基)銅、雙(8-羥基喹啉根基)錳、三(8-羥基喹啉根基)鋁、三(2-甲基-8-羥基喹啉根基)鋁、三(8-羥基喹啉根基)鎵、雙(10-羥基苯并[h]喹啉根基)鈹(bis(10-hydroxybenzo[h]quinolinato)beryllium)、雙(10-羥基苯并[h]喹啉根基)鋅、雙(2-甲基-8-喹啉根基)氯鎵、雙(2-甲基-8-喹啉根基)(鄰甲酚根基)鎵(bis(2-methyl-8-quinolinato)(o-cresolato)gallium)、雙(2-甲基-8-喹啉根基)(1-萘酚根基)鋁(bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum)、雙(2-甲基-8-喹啉根基)(2-萘酚根基)鎵以及類似化合物,但不限於此。
根據本發明的有機發光裝置根據所使用的材料可為前側發光型、後側發光型或雙側發光型。
另外,由化學式1表示的化合物可包含於除有機發光裝置以外的有機太陽能電池或有機電晶體中。
由化學式1表示的化合物的製備及包括此化合物的有機發光裝置將在以下實例中詳細描述。然而,這些實例僅出於說明的目的呈現,且不意欲限制本發明的範疇。
[實例]
實例1:製備化合物1
化合物A(7.50公克(g),20.05毫莫耳(mmol))及化
合物a-1(7.43公克,21.06毫莫耳)在500毫升(ml)圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(240毫升)中,向其添加2M水性碳酸鉀溶液(120毫升)且添加四-(三苯膦)鈀(0.70公克,0.60毫莫耳),且隨後將所得混合物加熱且攪拌4小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用四氫呋喃(180毫升)再結晶以製備化合物1(8.76公克,產率:67%)。
MS:[M+H]+=648
實例2:製備化合物2
化合物A(6.50公克,17.38毫莫耳)及化合物a-2(6.44公克,18.25毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(260毫升)中,向其添加2M水性碳酸鉀溶液(130毫升)且添加四-(三苯膦)鈀(0.60公克,0.52毫莫耳),且隨後將所得混合物加熱且攪拌3小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(270毫升)再結晶以製備化合物2(7.46公克,產率:66%)。
MS:[M+H]+=648
實例3:製備化合物3
化合物A(8.50公克,22.73毫莫耳)及化合物a-3(8.42公克,23.86毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(240毫升)中,向其添加2M水性碳酸鉀溶液(120毫升)且添加四-(三苯膦)鈀(0.79公克,0.68毫莫耳),且隨後將所得混合物加熱且攪拌2小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(210毫升)再結晶以製備化合物3(7.89公克,產率:54%)。
MS:[M+H]+=647
實例4:製備化合物4
化合物A(7.50公克,20.05毫莫耳)及化合物a-4(9.03公克,21.06毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(220毫升)中,向其添加2M水性碳酸鉀溶液(110毫升)且添加四-(三苯膦)鈀(0.70公克,0.60毫莫耳),且隨後將所得混合物加熱且攪拌5小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(220毫升)再結晶以製備化合物4(9.11公克,產率:63%)。
MS:[M+H]+=724
實例5:製備化合物5
化合物A-1(15.58公克,33.43毫莫耳)及化合物a-5(8.50公克,31.84毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(240毫升)中,向其添加2M水性碳酸鉀溶液(120毫升)且添加四-(三苯膦)鈀(1.10公克,0.96毫莫耳),且隨後將所得混合物加熱且攪拌4小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(280毫升)再結晶以製備化合物5(11.24公克,產率:62%)。
MS:[M+H]+=572
實例6:製備化合物6
化合物A-1(12.13公克,26.02毫莫耳)及化合物a-6(8.50公克,24.78毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(260毫升)中,向其添加2M水性碳酸鉀溶液(130毫升)且添加四-(三苯膦)鈀(0.86公克,0.74毫莫耳),且隨後將所得混合物加熱且攪拌5小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯
(270毫升)再結晶以製備化合物6(10.67公克,產率:66%)。
MS:[M+H]+=648
實例7:製備化合物7
化合物A-1(10.28公克,22.06毫莫耳)及化合物a-7(7.50公克,21.01毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(280毫升)中,向其添加2M水性碳酸鉀溶液(140毫升)且添加四-(三苯膦)鈀(0.73公克,0.63毫莫耳),且隨後將所得混合物加熱且攪拌5小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(310毫升)再結晶以製備化合物7(8.84公克,產率:64%)。
MS:[M+H]+=662
實例8:製備化合物8
化合物B(8.50公克,23.81毫莫耳)及化合物a-1(11.65公克,25.01毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(280毫升)中,向其添加2M水性碳酸鉀溶液(140毫升)且添加四-(三苯膦)鈀(0.83公克,0.71毫莫耳),且隨後將所得混合物加熱且攪拌4小時。將溫度降至常溫,移除水層,且所
得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(280毫升)再結晶以製備化合物8(10.22公克,產率:65%)。
MS:[M+H]+=648
實例9:製備化合物9
化合物B-1(10.70公克,22.96毫莫耳)及化合物a-6(7.50公克,21.87毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(180毫升)中,向其添加2M水性碳酸鉀溶液(90毫升)且添加四-(三苯膦)鈀(0.76公克,0.66毫莫耳),且隨後將所得混合物加熱且攪拌4小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(280毫升)再結晶以製備化合物9(8.71公克,產率:60%)。
MS:[M+H]+=650
實例10:製備化合物10
化合物C(9.50公克,22.73毫莫耳)及化合物a-8(9.62公克,23.86毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(260毫升)中,向其添加2M水性碳酸鉀溶液(130
毫升)且添加四-(三苯膦)鈀(0.79公克,0.68毫莫耳),且隨後將所得混合物加熱且攪拌4小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(240毫升)再結晶以製備化合物10(9.82公克,產率:62%)。
MS:[M+H]+=698
實例11:製備化合物11
化合物C-1(8.51公克,21.11毫莫耳)及化合物a-9(4.63公克,9.91毫莫耳)在500毫升圓底燒瓶中在氮氣氛圍下完全溶解於四氫呋喃(260毫升)中,向其添加2M水性碳酸鉀溶液(130毫升)且添加四-(三苯膦)鈀(0.70公克,0.60毫莫耳),且隨後將所得混合物加熱且攪拌5小時。將溫度降至常溫,移除水層,且所得產物經無水硫酸鎂乾燥,且隨後在減壓下濃縮,且用乙酸乙酯(310毫升)再結晶以製備化合物11(7.85公克,產率:58%)。
MS:[M+H]+=678
[實驗實例]
實驗實例1
將玻璃基底放入蒸餾水,且經超音波清潔,在所述玻璃基底上將氧化銦錫(indium tin oxide;ITO)塗佈成厚度為1,000埃(Å)的薄膜,在所述蒸餾水中溶解清潔劑。在此情況下,使用由費歇爾公司(Fischer Co.)製造的產品作為清潔劑,且使用由密理
博公司(Millipore Co.)製造的過濾器(filter)過濾兩次的蒸餾水用作蒸餾水。在將ITO清潔30分鐘之後,使用蒸餾水重複進行兩次歷時10分鐘的超音波清潔。在用蒸餾水完成清潔之後,基底用異丙醇、丙酮以及甲醇的溶劑超音波清潔,隨後乾燥,且隨後轉移至電漿清潔器。另外,基底使用氧電漿清潔5分鐘,且隨後轉移至真空沈積器。
在由此製備陽極電極的ITO透明電極上,以下化合物HI1及以下化合物HI2以98:2的比率(莫耳比)熱真空沈積成具有100埃的厚度,由此形成電洞注入層。以下化合物HT1在電洞注入層上真空沈積成厚度為1150埃以形成電洞傳輸層。以下化合物EB1在電洞傳輸層上真空沈積成厚度為50埃以形成電子阻擋層。隨後,以下化合物BH及以下化合物BD以25:1的重量比在電子阻擋層上真空沈積成厚度為200埃以形成發光層。以上實例1中所製備的化合物1在發光層上真空沈積成厚度為50埃以形成電洞阻擋層。以下化合物EI1及以下化合物LiQ以1:1的比率在電洞阻擋層上真空沈積成厚度為310埃以形成電子注入及傳輸層。氟化鋰(LiF)及鋁在電子注入及傳輸層上分別依序沈積成具有12埃及1,000埃的厚度,由此形成陰極。
在以上所提及的製程中,有機材料的氣相沈積速率保持在0.4埃/秒(Å/sec)至0.7埃/秒,陰極的氟化鋰及鋁的沈積速率分別保持在0.3埃/秒及在2埃/秒,且在沈積期間真空度保持在2×10-7托(torr)至5×10-6托,由此製造有機發光裝置。
實驗實例2至實驗實例11
除了使用以下表1中所繪示的化合物代替化合物1以外,以與實例1中相同的方式製造有機發光裝置。
比較實驗實例1至比較實驗實例3
電壓、效率、色彩座標以及使用壽命藉由將電流施加至有機發光裝置來量測,所述有機發光裝置在實驗實例及比較實驗實例中製造,且結果在以下表1中繪示。此時,T95意指亮度減小至初始亮度(1600尼特(nit))的95%所需要的時間。
如表1中所繪示,使用本發明的化合物作為電子阻擋層的有機發光裝置就有機發光裝置的效率、驅動電壓以及穩定性而言顯現極佳特徵。特定言之,與使用化合物HB2及化合物HB3製
造的比較實驗實例2及比較實驗實例3的有機發光裝置相比,在所述化合物中三嗪取代基鍵聯至9,9'-螺二[氟](9,9'-spirobi[fluorine])及9,9-二苯基-9H-芴(9,9-diphenyl-9H-fluorene)芯,使用本發明的化合物的實驗實例1至實驗實例11的有機發光裝置顯現低壓、高效以及長使用壽命特徵。另外,使用化合物HB-1製造的比較實驗實例1的有機發光裝置不顯現這些特徵,所述化合物具有取代胺類取代基的本發明的核心的結構。
1:基底
2:陽極
3:有機材料層
4:陰極
Claims (9)
- 一種化合物,由以下化學式1表示:
- 如申請專利範圍第1項所述的化合物,其中L為單鍵、伸苯基或咔唑二基。
- 如申請專利範圍第1項所述的化合物,其中Ar1及Ar2各自獨立地為苯基、聯苯基、聯三苯基、萘基、菲基、聯伸三苯基、二苯并呋喃基、二苯并噻吩基或9-苯基-9H-咔唑基。
- 如申請專利範圍第1項所述的化合物,其中Ar3為苯基、聯苯基或萘基。
- 如申請專利範圍第1項所述的化合物,其中Ar4為氫、苯基、聯苯基或萘基。
- 如申請專利範圍第1項所述的化合物,其中Ar5為苯基。
- 一種有機發光裝置,包括:第一電極;與所述第一電極相對設置的第二電極;以及設置於所述第一電極與所述第二電極之間的一或多個有機材料層,其中所述有機材料層中的一或多個層包括如申請專利範圍第1項至第8項中任一項所述的化合物。
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