CN115246777B - 有机化合物、混合物、组合物及有机电子器件 - Google Patents
有机化合物、混合物、组合物及有机电子器件 Download PDFInfo
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- CN115246777B CN115246777B CN202110488786.6A CN202110488786A CN115246777B CN 115246777 B CN115246777 B CN 115246777B CN 202110488786 A CN202110488786 A CN 202110488786A CN 115246777 B CN115246777 B CN 115246777B
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- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- YCBSHDKATAPNIA-UHFFFAOYSA-N non-3-ene Chemical compound CCCCCC=CCC YCBSHDKATAPNIA-UHFFFAOYSA-N 0.000 description 1
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- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
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- 235000011056 potassium acetate Nutrition 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
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- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- 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
- 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
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/22—Luminous paints
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Abstract
本发明涉及一种有机化合物、混合物、组合物及有机电子器件。该有机化合物具有式(1)所示结构,可有效提高器件的发光效率和寿命。
Description
技术领域
本发明涉及有机电致发光材料技术领域,特别是涉及一种有机化合物、混合物、组合物及有机电子器件。
背景技术
有机光电材料在合成上具有多样性,制造成本相对较低以及优良的光学与电学性能。有机发光二极管(OLED)在光电器件(例如平板显示器和照明)的应用方面具有广视角、反应时间快、工作电压低、面板厚度薄等优势,因而具有广阔的发展潜力。
有机电致发光现象是指利用有机物质将电能转化为光能的现象。利用有机电致发光现象的有机电致发光元件通常具有正极与负极以及在它们中间包含有机功能层的结构。为了提高有机电致发光元件的效率与寿命,有机功能层具有多层结构,每一层包含有不同的有机物质。具体的,可以包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等。在这种有机电致发光元件中,在两个电极之间施加电压,则由正极向有机功能层注入空穴,由负极向有机功能层注入电子,当注入的空穴与电子相遇时形成激子,该激子跃迁回基态时发出光。这种有机电致发光元件具有自发光、高亮度、高效率、低驱动电压、广视角和高对比度等特性。
OLED器件除了发光层之外,还需要空穴传输层、发光辅助层等涉及空穴传输的有机功能层,以便实现空穴、电子的平衡传输,以提高器件的效率和寿命。因此,除了开发高性能的发光层材料外,相应的空穴传输材料的开发也很重要,特别是应用于高效红光OLED器件的新型空穴传输材料。
发明内容
本发明的目的在于提供一类基于1,2-二氢苊(1,2-dihydroacenaphthylene)的有机化合物,可作为一类新型的空穴传输材料用于OLED器件中,提高器件的稳定性、效率和寿命。
本发明的技术方案如下:
一种有机化合物,具有如式(1)所的结构:
其中:
L1、L2分别独立选自单键,或取代或未取代的环原子数为6至40的芳香基团,或取代或未取代的环原子数为5至40的杂芳香基团;
Ar1、Ar2分别独立选自取代或未取代环原子数为6至40的芳香基团,或取代或未取代环原子数为5至40的杂芳香基团或非芳香环系。
本发明还提供一种混合物,所述混合物包括上述的有机化合物,及至少一种有机功能材料,所述有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、发光材料、主体材料和有机染料中的至少一种。
本发明还提供一种组合物,所述组合物包括上述的有机化合物,或上述的混合物,及至少一种有机溶剂。
本发明还提供一种有机电子器件,包含第一电极、第二电极、位于第一电极和第二电极之间的一个或多个有机功能层,所述有机功能层包含上述的有机化合物,或上述的混合物,或由上述的组合物制备而成。
与现有技术相比,本发明具有如下有益效果:
本发明提供的有机化合物,胺基上含有1,2-二氢苊(1,2-dihydroacenaphthylene)取代的萘基,1,2-二氢苊基团具有非完全共轭的五元环结构,萘基为共轭基团,通过非共轭基团与共轭基团的分子间相互作用从而改善材料空穴的传输性能。将本发明的有机化合物作为空穴传输材料用于有机电子器件中,可以实现较为平衡的空穴、电子传输,进而实现高效的载流子利用,提高器件的发光效率和寿命。
说明书如图
图1是本发明器件实施例1所示的OLED器件示意图;
其中,1是基板,2是阳极,3是空穴注入层,4是第一空穴传输层,5是第二空穴传输层,6是发光层,7是电子传输层,8是电子注入层,9是阴极。
具体实施方式
以下结合具体实施例和附图对本发明作进一步详细的说明。本发明可以以许多不同的形式来实现,并不限于本文所描述的实施方式。相反地,提供这些实施方式的目的是使对本发明公开内容理解更加透彻全面。
除非另有定义,本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施例的目的,不是旨在于限制本发明。本文所使用的术语“和/或”包括一个或多个相关的所列项目的任意的和所有的组合。
在本发明中,“取代”表示被取代基中的氢原子被取代基所取代。
在本发明中,同一取代基多次出现时,可独立选自不同基团。如通式含有多个R1,则R1可独立选自不同基团。例如苯环上6个R1可以彼此相同或不同。
本发明中,“取代或未取代”表示所定义的基团可以被取代,也可以不被取代。当所定义的基团被取代时,应理解为任选被本领域可接受的基团所取代,包括但不限于:C1-30烷基、含有3-20个环原子的杂环基、含有5-20个环原子的芳基、含有5-20个环原子的杂芳基、硅烷基、羰基、烷氧基羰基、芳氧基羰基、氨基甲酰基、卤甲酰基、甲酰基、-NRR′、氰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、三氟甲基、硝基或卤素,且上述基团也可以进一步被本领域可接受取代基取代;可理解的,-NRR′中的R和R′各自独立地为本领域可接受的基团所取代,包括但不限于H、C1-6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、含有5-20个环原子的芳基或含有5-10个环原子的杂芳基;所述C1-6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、含有5-20个环原子的芳基或含有5-10个环原子的杂芳基任选进一步被一个或多个以下基团取代:C1-6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、卤素、羟基、硝基或氨基。
在本发明中,“环原子数”表示原子键合成环状而得到的结构化合物(例如,单环化合物、稠环化合物、交联化合物、碳环化合物、杂环化合物)的构成该环自身的原子之中的原子数。该环被取代基所取代时,取代基所包含的原子不包括在成环原子内。关于以下所述的“环原子数”,在没有特别说明的条件下也是同样的。例如,苯环的环原子数为6,萘环的环原子数为10,噻吩基的环原子数为5。
在本发明中,“烷基”可以表示直链、支链和/或环状烷基。烷基的碳数可以为1至50、1至30、1至20、1至10或1至6。包含该术语的短语,例如,“C1-9烷基”是指包含1~9个碳原子的烷基,每次出现时,可以互相独立地为C1烷基、C2烷基、C3烷基、C4烷基、C5烷基、C6烷基、C7烷基、C8烷基或C9烷基。烷基的非限制性实例包括甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、2-乙基丁基、3,3-二甲基丁基、正戊基、异戊基、新戊基、叔戊基、环戊基、1-甲基戊基、3-甲基戊基、2-乙基戊基、4-甲基-2-戊基、正己基、1-甲基己基、2-乙基己基、2-丁基己基、环己基、4-甲基环己基、4-叔丁基环己基、正庚基、1-甲基庚基、2,2-二甲基庚基、2-乙基庚基、2-丁基庚基、正辛基、叔辛基、2-乙基辛基、2-丁基辛基、2-己基辛基、3,7-二甲基辛基、环辛基、正壬基、正癸基、金刚烷基、2-乙基癸基、2-丁基癸基、2-己基癸基、2-辛基癸基、正十一烷基、正十二烷基、2-乙基十二烷基、2-丁基十二烷基、2-己基十二烷基、2-辛基十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、2-乙基十六烷基、2-丁基十六烷基、2-己基十六烷基、2-辛基十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基、2-乙基二十烷基、2-丁基二十烷基、2-己基二十烷基、2-辛基二十烷基、正二十一烷基、正二十二烷基、正二十三烷基、正二十四烷基、正二十五烷基、正二十六烷基、正二十七烷基、正二十八烷基、正二十九烷基、正三十烷基、金刚烷等。
“芳基、芳香基或芳香基团”指至少包含一个芳环的烃基。“杂芳香基或杂芳香基团”指包含至少一个杂原子的芳香烃基。杂原子优选选自Si、N、P、O、S和/或Ge,特别优选选自Si、N、P、O和/或S。稠环芳香基团指芳香基团的环可以具有两个或多个环,其中两个碳原子被两个相邻的环共用,即稠环。稠杂环芳香基团指包含至少一个杂原子的稠环芳香烃基。对于本发明的目的,芳香基团或杂芳香基团不仅包括芳香环的体系,而且包含非芳香族的环系。因此,比如吡啶、噻吩、吡咯、吡唑、三唑、咪唑、噁唑、噁二唑、噻唑、四唑、吡嗪、哒嗪、嘧啶、三嗪、卡宾等体系,对于该发明目的同样认为是芳香基团或杂环芳香基团。对于本发明的目的,稠环芳香族或稠杂环芳香族环系不仅包括芳香基团或杂芳香基团的体系,而且,其中多个芳香基团或杂环芳香基团也可以被短的非芳族单元间断(<10%的非H原子,优选小于5%的非H原子,比如C、N或O原子)。因此,比如9,9'-螺二芴,9,9-二芳基芴,三芳胺,二芳基醚等体系,对于该发明目的同样认为是稠环芳香族环系。
在某个优选的实施例中,所述的芳香基团选自:苯、萘、蒽、荧蒽、菲、苯并菲、二萘嵌苯、并四苯、芘、苯并芘、苊、芴、及其衍生物;杂芳香基团选自三嗪、吡啶、嘧啶、咪唑、呋喃、噻吩、苯并呋喃、苯并噻吩、吲哚、咔唑、吡咯并咪唑、吡咯并吡咯、噻吩并吡咯、噻吩并噻吩、呋喃并吡咯、呋喃并呋喃、噻吩并呋喃、苯并异噁唑、苯并异噻唑、苯并咪唑、喹啉、异喹啉、邻二氮萘、喹喔啉、菲啶、伯啶、喹唑啉、喹唑啉酮、二苯并噻吩、二苯并呋喃、咔唑及其衍生物。
“胺基”是指胺的衍生物,具有式-N(X)2的结构特征,其中每个“X”独立地是H、取代的或未被取代的烷基、取代的或未被取代的环烷基、取代的或未被取代的杂环基等。胺基的非限制性类型包括-NH2、-N(烷基)2、-NH(烷基)、-N(环烷基)2、-NH(环烷基)、-N(杂环基)2、-NH(杂环基)、-N(芳基)2、-NH(芳基)、-N(烷基)(芳基)、-N(烷基)(杂环基)、-N(环烷基)(杂环基)、-N(芳基)(杂芳基)、-N(烷基)(杂芳基)等。
本发明中,与单键相连的“*”表示连接位点。
本发明中,基团中未指明连接位点时,表示基团中任选可连接位点作为连接位点;
本发明中,基团中未指明稠合位点时,表示基团中任选可稠合位点作为稠合位点,优选基团中处于邻位的两个或多个位点为稠合位点;
本发明中,取代基相连的单键贯穿相应的环,表述该取代基可与环的任选位置连接,例如中R与苯环的任一可取代位点相连。如/>表示可与/>中苯环上任选位置形成并环,优选苯环上相邻的C原子。
在本发明中,“成环”的意思是形成脂肪族环、芳香族环、杂芳香族环、脂肪族杂环或它们组合后的形态。
本发明的技术方案如下:
一种有机化合物,具有如式(1)所的结构:
其中:
L1、L2分别独立选自单键,或取代或未取代的环原子数为6至40的芳香基团,或取代或未取代的环原子数为5至40的杂芳香基团;
Ar1、Ar2分别独立选自取代或未取代环原子数为6至40的芳香基团,或取代或未取代环原子数为5至40的杂芳香基团或非芳香环系。
在一实施例中,所述有机化合物具有式(1-1)-(1-3)任一所示的结构:
在一实施例中,所述有机化合物选自式(1-1),可能原因在于:芳胺基团和1,2-二氢苊基团在萘上邻位连接,使得两个基团之间具有较大的位阻,限制了取代基的转动,使分子具有较大的刚性,从而改善了分子的堆积,增加了器件的效率、稳定性和寿命。
在一实施例中,Ar1、Ar2分别独立选自取代或未取代环原子数为6至18的芳香基团,或取代或未取代环原子数为5至18的杂芳香基团;进一步,Ar1、Ar2分别独立选自未取代的环原子数为6至18的芳香基团,或被R取代的环原子数为6至18的芳香基团,或未取代环原子数为5至18的杂芳香基团,或被R取代的环原子数为5至18的杂芳香基团;其中:R选自-D,具有1至20个C原子的直链烷基,具有3至20个C原子的支链或环状的烷基,环原子数为6至10的芳香基团,环原子数为5至13的杂芳香基团。
在一实施例中,所述的Ar1和Ar2分别独立选自(B-1)-(B-6)中的任意一种:
其中:
X1选自N或CR1;
Y1选自O、S、S=O、SO2、NR2、PR2、CR2R3或SiR2R3;
R1,R2,R3每次出现时,分别独立选自:-H,-D,具有1至20个C原子的直链烷基,具有1至20个C原子的直链烷氧基,具有1至20个C原子的直链硫代烷氧基,具有3至20个C原子的支链或环状的烷基,具有3至20个C原子的支链或环状的烷氧基,具有3至20个C原子的支链或环状的硫代烷氧基,甲硅烷基,具有1至20个C原子的酮基,具有2至20个C原子的烷氧基羰基,具有7至20个C原子的芳氧基羰基,氰基,氨基甲酰基,卤甲酰基,甲酰基,异氰基,异氰酸酯基,硫氰酸酯基,异硫氰酸酯基,羟基、硝基,CF3、Cl、Br、F、可交联的基团,取代或未取代的环原子数为6至60的芳香基团,取代或未取代的环原子数为5至60的杂芳香基团,取代或未取代的环原子数为5至60的芳氧基,具有5至60个环原子的杂芳氧基基团,或这些基团的组合;
相邻的R2和R3相互连接成环或不成环;
Ar3选自取代或未取代的环原子数为6至20的芳香基团,或取代或未取代的环原子数为5至20的杂芳香基团。
可以理解地,在本发明中,当X1与L1或L2连接时,X1为C。
优选地,X1均选自CR1。
更优选地,所述的R1每次出现时,独立地选自-H、-D、或具有1至20个C原子的直链烷基、或具有3至20个C原子的支链或环状的烷基、或苯基、或萘基。
进一步,R1每次出现时,独立地选自-H、-D、或具有3至10个C原子的环状的烷基。
更优选地,至少有一个R1选自3至10个C原子的环状的烷基。
进一步地,所述环状的烷基选自以下基团:
进一步优选地,至少有一个R1选自环己烷基或金刚烷基。
在一实施例中,R2和R3分别独立选自-H、-D、或具有1至10个C原子的直链烷基、或具有3至10个C原子的支链或环状的烷基、或苯基、或萘基。
优选地,R2和R3不成环或相互连接成具有5至20个环原子的脂肪环或杂芳环,或6至20个环原子的芳环。特别优选地,R2和R3不成环或相互连接成环己烷基或金刚烷基。
在一实施例中,所述的Ar3选自以下基团中的任意一种:
进一步地,所述的(B-3)选自以下基团中的任意一种:
优选地,所述的Ar1、Ar2分别独立选自以下基团中的任意一种:
*表示Ar1与L1,Ar2与L2的连接位点;n选自0,1,2,3或4。
在一实施例中,L1、L2分别独立选自单键,或取代或未取代的环原子数为6至10的芳香基团或取代或未取代的环原子数为5至10的杂芳香基团;优选地,L1、L2分别独立地选自单键,亚苯基或联苯基。
特别优选地,通式(1)中的选自如下任一所示的基团:
优选地,n选自0或1或2;
进一步,L1、L2分别独立地选自单键,亚苯基或联苯基,在一实施例中,L1、L2选自单键或苯基;更进一步,L1、L2选自单键或在一实施例中,L1、L2均选自单键或L1、L2均选自/>
进一步,R1每次出现时,独立地选自-H、-D、或具有3至10个C原子的环状的烷基。
在一实施例中,本发明所述有机化合物具有式(2-1)-(2-9)任一所示的结构:
在一实施例中,式(2-1)-(2-9)中的R1每次出现时,独立地选自-H、-D、或具有1至20个C原子的直链烷基、或具有3至20个C原子的支链或环状的烷基、或苯基、或萘基。
进一步,式(2-1)-(2-9)中R1每次出现时,独立地选自-H、-D、或具有1至10个C原子的直链烷基、或具有3至10个C原子的支链或环状的烷基、或苯基、或萘基。
在一实施例中,式(2-1)-(2-9)中L1、L2分别独立地选自单键,亚苯基或联苯基,在一实施例中,L1、L2选自单键或苯基;更进一步,L1、L2选自单键或在一实施例中,L1、L2均选自单键或L1、L2均选自/>
按照本发明所述的有机化合物,选自但不限于以下结构,且这些结构上的H可以被任意取代:
/>
/>
/>
按照本发明的有机化合物,可以作为功能材料用于电子器件的功能层中。有机功能层包括,但不限于,空穴注入层(HIL),空穴传输层(HTL),电子传输层(ETL),电子注入层(EIL),电子阻挡层(EBL),空穴阻挡层(HBL),发光层(EML)。
在一实施例中,按照本发明所述的有机化合物用于空穴传输层中。
本发明进一步涉及一种混合物,包含有至少一种以上所述的有机化合物,及至少另一种有机功能材料,所述至少另一种的有机功能材料可选于空穴注入材料(HIM),空穴传输材料(HTM),电子传输材料(ETM),电子注入材料(EIM),电子阻挡材料(EBM),空穴阻挡材料(HBM),发光材料(Emitter),主体材料(Host)和有机染料。例如在WO2010135519A1,US20090134784A1和WO 2011110277A1中对各种有机功能材料有详细的描述,特此将此3专利文件中的全部内容并入本文作为参考。
在一实施例中,所述另一种有机功能材料选自电子传输材料,作为共主体运用于电子器件中。
本发明还涉及一种组合物,包含至少一种如上所述的有机化合物或混合物,及至少一种有机溶剂;所述的至少一种的有机溶剂选自芳族或杂芳族、酯、芳族酮或芳族醚、脂肪族酮或脂肪族醚、脂环族或烯烃类化合物,或硼酸酯或磷酸酯类化合物,或两种及两种以上溶剂的混合物。
在一个优选的实施例中,按照本发明的一种组合物,所述的至少的一种有机溶剂选自基于芳族或杂芳族的溶剂。
适合本发明的基于芳族或杂芳族溶剂的例子有,但不限制于:对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、环己基苯、苄基丁基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-三氯苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、N-甲基二苯胺、4-异丙基联苯、α,α-二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘、喹啉、异喹啉、2-呋喃甲酸甲酯、2-呋喃甲酸乙酯等;
适合本发明的基于芳族酮溶剂的例子有,但不限制于:1-四氢萘酮,2-四氢萘酮,2-(苯基环氧)四氢萘酮,6-(甲氧基)四氢萘酮,苯乙酮、苯丙酮、二苯甲酮、及它们的衍生物,如4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮、2-甲基苯丙酮等;
适合本发明的基于芳族醚溶剂的例子有,但不限制于:3-苯氧基甲苯、丁氧基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本乙醚、1,3-二丙氧基苯、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚;
在一些优选的实施例中,按照本发明的组合物,所述的至少一种的有溶剂可选自:脂肪族酮,例如,2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、葑酮、佛尔酮、异佛尔酮、二正戊基酮等;或脂肪族醚,例如,戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚等。
在另一些优选的实施例中,按照本发明的组合物,所述的至少一种的有溶剂可选自基于酯的溶剂:辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯、油酸烷酯等。特别优选辛酸辛酯、癸二酸二乙酯、邻苯二甲酸二烯丙酯、异壬酸异壬酯。
所述的溶剂可以是单独使用,也可以是作为两种或多种有机溶剂的混合物使用。
在某些优选的实施例中,按照本发明的一种组合物,包含至少一种如上所述的有机化合物或高聚物或混合物及至少一种有机溶剂,还可进一步包含另一种有机溶剂。另一种有机溶剂的例子包括(但不限于):甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷、茚和/或它们的混合物。
一些优选的实施例中,特别适合本发明的溶剂是汉森(Hansen)溶解度参数在以下范围内的溶剂:
δd(色散力)在17.0~23.2MPa1/2的范围,尤其是在18.5~21.0MPa1/2的范围;
δp(极性力)在0.2~12.5MPa1/2的范围,尤其是在2.0~6.0MPa1/2的范围;
δh(氢键力)在0.9~14.2MPa1/2的范围,尤其是在2.0~6.0MPa1/2的范围。
按照本发明的组合物,其中有机溶剂在选取时需考虑其沸点参数。本发明中,所述的有机溶剂的沸点≥150℃;优选为≥180℃;较优选为≥200℃;更优为≥250℃;最优为≥275℃或≥300℃。这些范围内的沸点对防止喷墨印刷头的喷嘴堵塞是有益的。所述的有机溶剂可从溶剂体系中蒸发,以形成包含功能材料薄膜。
在一个优选的实施方案中,按照本发明的组合物是一溶液。
在另一个优选的实施方案中,按照本发明的组合物是一悬浮液。
本发明实施例中的组合物中可以包括0.01wt%至10wt%的按照本发明的化合物或混合物,较好的是0.1wt%至15wt%,更好的是0.2wt%至5wt%,最好的是0.25wt%至3wt%。
本发明还涉及所述组合物作为涂料或印刷油墨在制备有机电子器件时的用途,特别优选的是通过打印或涂布的制备方法。
其中,适合的打印或涂布技术包括(但不限于)喷墨打印,活版印刷,丝网印刷,浸涂,旋转涂布,刮刀涂布,辊筒印花,扭转辊印刷,平版印刷,柔版印刷,轮转印刷,喷涂,刷涂或移印,狭缝型挤压式涂布等。首选的是凹版印刷,喷印及喷墨印刷。溶液或悬浮液可以另外包括一个或多个组份例如表面活性化合物,润滑剂,润湿剂,分散剂,疏水剂,粘接剂等,用于调节粘度,成膜性能,提高附着性等。有关打印技术,及其对有关溶液的相关要求,如溶剂及浓度,粘度等。
本发明还提供一种如上所述的有机化合物、混合物或组合物在有机电子器件中的应用,所述的有机电子器件可选于,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic Plasmon EmittingDiode)等,特别优选为OLED。本发明实施例中,优选将所述有机化合物用于OLED器件的空穴传输层。
本发明进一步涉及一种有机电子器件,包含第一电极、第二电极、位于第一电极和第二电极之间的一个或多个有机功能层,所述有机功能层包含如上所述的有机化合物、混合物或由上述的组合物制备而成。进一步地,所述有机电子器件,包含阴极、阳极和位于阴极和阳极的一个或多个有机功能层。
所述的有机电子器件可选于,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic Plasmon EmittingDiode)等,特别优选的是有机电致发光器件,如OLED,OLEEC,有机发光场效应管。
按照本发明所述的有机功能层可选自空穴注入层(HIL)、空穴传输层(HTL)、发光层(EML)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)。适合用于这些功能层中的材料在上面及在WO2010135519A1、US20090134784A1和WO2011110277A1中有详细的描述,特此将此3篇专利文件中的全部内容并入本文作为参考。
在一实施例中所述有机功能层至少包含一空穴传输层或电子阻挡层,所述空穴传输层或电子阻挡层包含如上所述的有机化合物。具体有机化合物的定义如前文所述。
在一些更加优选的实施例中,所述有机功能层至少包含两个空穴传输层,其中紧靠发光层的空穴传输层(第二空穴传输层)包含如上所述的有机化合物。
在一实施例中,按照本发明所述的有机电子器件,是一红光有机电子器件。
在一实施例中,按照本发明所述的有机电子器件,包含第一电极、第二电极、位于第一电极和第二电极之间的一个或多个有机功能层,所述功能层至少包含两个功能层:其中一个是空穴传输层或者电子阻挡层,该功能层包含如上所述的有机化合物;另一个功能层是发光层,发光层材料选自如通式(5)所示的结构:
其中:
q选自1或2;
Ar4多次出现时,独立选自取代或未取代的环原子数为5至40的杂芳香基团;
Ar5多次出现时,独立选自取代或未取代的环原子数为6至40的芳香基团,或取代或未取代的环原子数为5至40的杂芳香基团;
R4-R5每次出现时,分别独立选自:-H,-D,具有1至20个C原子的直链烷基,具有3至20个C原子的支链或环状的烷基,取代或未取代的环原子数为5至60的芳香基团,取代或未取代的环原子数为5至60的杂芳香基团,或这些基团的组合。
在一实施例中,Ar4多次出现时,独立选自喹啉或异喹啉及其衍生物。
在一实施例中,Ar5多次出现时,独立选自苯基及其衍生物。
优选地,通式(5)选自通式(6-1)-(6-3)任一结构:
其中:
a选自0-6的任一整数,b选自0-4的任一整数;
R6-R7每次出现时,分别独立选自:D,具有1至20个C原子的直链烷基,具有3至20个C原子的支链或环状的烷基,取代或未取代的环原子数为6至60的芳香基团,取代或未取代的环原子数为5至60的杂芳香基团,或这些基团的组合。
在一实施例中,至少一个R6或R7选自具有1至20个C原子的直链烷基或具有3至20个C原子的支链或环状的烷基。
在一实施例中,至少一个R6选自具有1至20个C原子的直链烷基或具有3至20个C原子的支链或环状的烷基。进一步,至少一个R7选自具有1至20个C原子的直链烷基或具有3至20个C原子的支链或环状的烷基。
按照通式(5)所述的金属配合物,优选自但不限于如下结构,这些结构可以被任意取代:
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按照本发明的发光器件,其发光波长在600到700nm之间,较好的是在600到650nm之间,更好的是在600到630nm之间。
本发明还涉及按照本发明的电致发光器件在各种电子设备中的应用,包含,但不限于,显示设备,照明设备,光源,传感器等等。
下面将结合优选实施例对本发明进行了说明,但本发明并不局限于下述实施例,应当理解,所附权利要求概括了本发明的范围在本发明构思的引导下本领域的技术人员应意识到,对本发明的各实施例进行的一定的改变,都将被本发明的权利要求书的精神和范围所覆盖。
具体实施例
1.化合物的合成
实施例1化合物1的合成
中间体1-2的合成:将1-1(60mmol),联硼酸频哪醇酯(60mmol),Pd(dppf)Cl2(0.2mmol)和醋酸钾(70mmol)加至180ml1,4-二氧六环中,在氮气环境中100℃搅拌8h。冷却后,旋蒸除去溶剂,二氯甲烷溶解剩余物并水洗分液,收集有机相,有机相旋蒸除去溶剂后,所得粗产品经重结晶得到中间体1-2,收率75%。
中间体1-4的合成:将化合物1-3(50mmol)溶于二氯甲烷(100ml)中。在0℃氮气环境中缓慢滴加三乙胺(80mmol)并搅拌30min;然后滴加三氟甲磺酸酐(124mmol),保持0℃搅拌5h。然后将反应液依次用水、饱和碳酸钠溶液、水洗涤,收集有机相。有机相旋蒸除去溶剂后柱层析得到中间体1-4,收率80%。
中间体1-5的合成:将中间体1-4(40mmol)、中间体1-2(40mmol)溶于1,4-二氧六环与水(200/20ml)的混合溶剂中,并加入Pd(PPh3)4(0.5mmol)和碳酸钾(70mmol)。在氮气环境下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后二氯甲烷萃取并水洗分液,收集有机相并旋蒸除去溶剂,所得粗产品经过柱层析得到中间体1-5,收率90%。
中间体1-6的合成:将中间体1-5(35mmol)、铁粉(175mmol)、氯化铵(190mmol)、盐酸(7.0ml)和甲醇/THF/水(100/100/40ml)混合溶剂的混合物升温至70℃搅拌。待反应完全,冷却后过滤,旋蒸除去大部分溶剂,剩余物用二氯甲烷溶解并用弱碱水洗涤至中性,分液,收集有机相并旋蒸除去溶剂,所得粗产品经过柱层析纯化后得到中间体1-6,收率75%。
中间体1-8的合成:将中间体1-6(25mmol)、化合物1-7(25mmol)、Pd(dba)2(0.5mmol)、三叔丁基膦(1.0mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气环境下75℃搅拌4h。冷却后水洗并分液,收集有机相,旋蒸除去溶剂,所得粗产品经过柱层析纯化得到中间体1-8,收率80%。
化合物1的合成:将中间体1-8(20mmol)、化合物1-9(20mmol)、Pd(dba)2(0.5mmol)、三叔丁基膦(1.0mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气环境下100℃搅拌6h。冷却后水洗并分液,收集有机相,旋蒸除去溶剂,所得粗产品经过柱层析、重结晶纯化得到化合物1,收率85%。MS(ASAP):639。
实施例2化合物2的合成
化合物2的合成:将中间体1-6(20mmol)、化合物1-9(40mmol)、Pd(dba)2(0.5mmol)、三叔丁基膦(1.0mmol)和叔丁醇钠(50mmol)溶于甲苯中,在氮气环境下100℃搅拌12h。冷却后水洗并分液,收集有机相,旋蒸除去溶剂,所得粗产品经过柱层析、重结晶纯化得到化合物2,收率90%。MS(ASAP):599。
实施例3化合物3的合成
化合物3的合成参照化合物1的合成,不同之处在于将1-9替换为3-1,收率80%。MS(ASAP):721。
实施例4化合物4的合成
中间体4-2的合成参照中间体1-8的合成,不同之处在于将1-7替换为4-1,收率75%。
化合物4的合成参照化合物1的合成,不同之处在于将1-8替换为4-2,并将1-9替换为4-3,收率70%。MS(ASAP):629。
实施例5化合物5的合成
化合物5的合成参照化合物1的合成,不同之处在于将1-8替换为4-2,收率85%。MS(ASAP):629。
实施例6化合物6的合成
中间体6-2的合成参照中间体1-8的合成,不同之处在于将1-7替换为6-1,收率70%。
化合物6的合成参照化合物1的合成,不同之处在于将1-9替换为6-3,收率85%。MS(ASAP):587。
实施例7化合物7的合成
中间体7-2的合成参照1-8的合成,不同之处在于将1-7替换为7-1,收率86%。
化合物7的合成参照化合物1的合成,不同之处在于将1-8替换为7-2,并将1-9替换为7-3,收率85%。MS(ASAP):639。
实施例8化合物8的合成
中间体8-2的合成参照中间体1-8的合成,不同之处在于将1-7替换为8-1,收率75%。
化合物8的合成参照化合物1的合成,不同之处在于将8-2替换为1-9,收率76%。MS(ASAP):623。
实施例9化合物9的合成
化合物9的合成参照化合物1的合成,不同之处在于将1-8替换为7-2,并将1-9替换为9-1,收率80%。MS(ASAP):669。
实施例10化合物10的合成
化合物10的合成参照化合物2的合成,不同之处在于将1-9替换为10-1,收率82%。MS(ASAP):715。
实施例11化合物11的合成
中间体11-2的合成:将化合物11-1(40mmol)、中间体1-2(40mmol)溶于1,4-二氧六环与水(200/20ml)的混合溶剂中,并加入Pd(PPh3)4(0.5mmol)和碳酸钾(70mmol)。在氮气环境下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后二氯甲烷萃取产物并水洗分液,收集有机相并旋蒸除去溶剂,所得粗产品经过柱层析纯化得到中间体11-2,收率89%。
化合物11的合成:将中间体11-2(30mmol)、化合物11-3(30mmol)、Pd(dba)2(0.7mmol)、三叔丁基膦(1.4mmol)和叔丁醇钠(40mmol)溶于甲苯中,在氮气环境下100℃搅拌12h。冷却后水洗并分液,收集有机相,旋蒸除去溶剂,所得粗产品经过柱层析、重结晶纯化得到化合物11,收率75%。MS(ASAP):599。
实施例12化合物12的合成
中间体12-2的合成:将中间体12-1(40mmol)、9-1(40mmol)、Pd(dba)2(0.5mmol)、三叔丁基膦(1mmol)和叔丁醇钠(60mmol)溶于甲苯中,在氮气环境下80℃搅拌6h。冷却后水洗并分液,收集有机相,旋蒸除去溶剂,所得粗产品经过柱层析、重结晶纯化得到中间体12-2,收率78%。
化合物12的合成参照化合物11的合成,不同之处在于将11-3替换为12-2,收率73%。MS(ASAP):629。
实施例13化合物13的合成
中间体13-2的合成参照12-2的合成,不同之处在于将12-1替换为13-1,并将9-1替换为4-3,收率75%。
化合物13的合成参照化合物11的合成,不同之处在于将11-3替换为13-2,收率70%。MS(ASAP):639。
实施例14化合物14的合成
中间体14-2的合成参照12-2的合成,不同之处在于将9-1替换为14-1,收率76%。
化合物14的合成参照化合物11的合成,不同之处在于将11-3替换为14-2,收率72%。MS(ASAP):732。
实施例15化合物15的合成
中间体15-2的合成参照11-2的合成,不同之处在于将11-1替换为15-1,收率85%。
化合物15的合成参照化合物11的合成,不同之处在于将11-2替换为15-2,收率75%。MS(ASAP):599。
实施例16化合物16的合成
中间体16-2的合成参照12-2的合成,不同之处在于将12-1替换为16-1,并将9-1替换为4-3,收率76%。
化合物16的合成参照化合物11的合成,不同之处在于将11-2替换为15-2,并将11-3替换为16-2,收率72%。MS(ASAP):673。
实施例17化合物17的合成
化合物17的合成参照化合物11的合成,不同之处在于将11-2替换为15-2,并将11-3替换为12-2,收率75%。MS(ASAP):629。
实施例18化合物18的合成
中间体18-1的合成参照12-2的合成,不同之处在于将9-1替换为1-7,收率77%。
化合物18的合成参照化合物11的合成,不同之处在于将11-2替换为15-2,并将11-3替换为18-1,收率76%。MS(ASAP):639。
实施例19化合物19的合成
中间体19-1的合成参照1-8的合成,不同之处在于将1-7替换为1-9,收率70%。
化合物19的合成参照化合物1的合成,不同之处在于将1-8替换为19-1,并将1-9替换为19-2,收率69%。MS(ASAP):821。
实施例20化合物20的合成
化合物20的合成参照化合物11合成,不同之处在于将11-2换为15-2,并将11-3替换为20-1,收率80%。MS(ASAP):559。
实施例21化合物21的合成
中间体21-2的合成参照12-2的合成,不同之处在于将9-1替换为21-1,收率75%。
中间体21的合成参照化合物11的合成,不同之处在于将11-3替换为21-2,收率78%。MS(ASAP):605。
实施例22化合物22的合成
中间体22的合成参照化合物2的合成,不同之处在于将1-9替换为22-1,收率80%。MS(ASAP):627。
实施例23化合物23的合成
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化合物23的合成参照化合物1的合成,不同之处在于将1-8替换为7-2,收率80%。MS(ASAP):639。
实施例24化合物24的合成
中间体24-1的合成参照1-8的合成,不同之处在于将1-7替换为9-1,收率75%。
化合物24的合成参照化合物1的合成,不同之处在于将1-8替换为24-1,收率85%。MS(ASAP):629。
实施例25化合物25的合成
化合物25的合成参照化合物11的合成,不同之处在于将11-3替换为18-1,收率80%。MS(ASAP):639。
实施例26化合物26的合成
中间体26-1的合成参照12-2的合成,不同之处在于将9-1替换为7-1,收率74%。
化合物26的合成参照化合物11的合成,不同之处在于将11-3替换为26-1,收率75%。MS(ASAP):639。
实施例27化合物27的合成
化合物27的合成参照化合物11的合成,不同之处在于将11-2替换为15-2,并将11-3替换为26-1。MS(ASAP):639。
实施例28化合物28的合成
化合物28的合成参照化合物1的合成,不同之处在于将1-8替换为19-1,并将1-9替换为溴苯,收率80%。MS(ASAP):523。
2.器件制备及检测
器件实施例1
器件结构为ITO/空穴注入层(10nm)/第一空穴传输层(60nm)/第二空穴传输层(60nm)/主体材料RH1:红光客体RD2/ETM:Liq/LiF/Al。其中主体材料RH1与RD2的质量比为95:5。具体的制备过程如下:
a、导电玻璃基片的清洗:首次使用时,可用多种溶剂进行清洗,例如氯仿、酮、异丙醇进行清洗,然后进行紫外臭氧等离子处理;
b、空穴注入层由HT1/HATCN(97/3,w/w)在ITO层上于高真空(1×10-6毫巴)中热蒸镀而成;
c、在空穴注入层上,蒸镀60nm厚的HT1作为第一空穴传输层;
d、在第一空穴传输层上,蒸镀60nm厚的本发明化合物1作为第二空穴传输层;
e、在第二空穴传输层上,真空蒸镀40nm的发光层;发光层包括RH1作为主体材料,RD2作为客体材料,两种材料采用多源共蒸;其中控制RD2的蒸镀速率为RH1的5%;
f、在发光层上,蒸镀厚度为25nm的ETM/Liq(1:1质量比)混合物作为电子传输层;电子传输层上,0.5nm的LiF作为电子注入层;150nm厚的Al作为阴极;
g、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
器件实施例1的器件结构如图1所示,其他OLED器件的结构与实施例一样,制备过程参照器件实施例1,不同之处在于将第二空穴传输层材料(化合物1)或红光客体材料RD2换成表1所示化合物。
各OLED器件的电流电压(J-V)特性通过表征设备来表征,同时记录重要的参数如效率,寿命及外部量子效率。表1是OLED器件寿命及外量子效率比较,其中的寿命LT95是在恒定电流下,亮度下降到初始亮度@1000nits的95%时的时间。这里LT95、外量子效率是相对于对比器件实施例1(对应材料对比例1)而计算的,即以对比器件实施例1的寿命为1,外量子效率为100。
表1 OLED器件性能比较
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通过表1可知,器件实施例1至实施例31的器件外量子效率和寿命明显高于对比器件实施例1(对应RD2和对比例1)、对比器件实施例2(对应RD1和对比例1)、对比器件实施例3(对应RD2,没有第二空穴传输层)和对比器件实施例4(对应RD2和对比例2)。
通过与对比器件实施例3对比可知,当本申请所述的化合物作为第二空穴传输层的材料存在于器件中时有助于提升器件性能,这可能是因为第二空穴传输层提高了空穴向发光层的注入效率,同时阻挡了电子从发光层扩散向空穴传输层,具备电子阻挡层的作用,从而提高了激子的利用效率;
通过与对比器件实施例1、2及4对比可知,本发明的有机化合物的空穴传输性能和电子阻挡性能明显优于对比例1及对比例2所示化合物。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (8)
1.一种有机化合物,其特征在于,具有如式(1)所的结构:
其中:
L1、L2分别独立选自单键、二苯并噻吩基;
Ar1、Ar2分别独立选自(B-1)-(B-3)、(B-5)-(B-6)中的任意一种:
X1选自CR1,R1选自-H、1-10个C原子的直链烷基、3-10个C原子的支链烷基、环己烷基或金刚烷基,Y1选自O、S、CR2R3,R2、R3分别独立选自具有1-10个碳原子的直链烷基或R2、R3相互连接成金刚烷基
Ar3选自以下基团:
Ar3中,X1选自CR1,R1选自-H。
2.根据权利要求1所述的有机化合物,其特征在于,其具有式(1-1)-(1-3)任一所示的结构:
3.根据权利要求1所述的有机化合物,其特征在于,所述的Ar1、Ar2分别独立选自以下基团中的任意一种:
*表示Ar1与L1,Ar2与L2的连接位点;n选自0、1、2、3或4。
4.根据权利要求3所述的有机化合物,其特征在于,通式(1)中的选自如下任一所示的基团:
5.根据权利要求4所述的有机化合物,其特征在于,具有式(2-1)-(2-9)任一所示的结构:
6.根据权利要求1所述的有机化合物,其特征在于,具有如下任一所示的结构:
7.一种组合物,其特征在于,包含如权利要求1-6任一项所述的有机化合物,及至少一种有机溶剂。
8.一种有机电子器件,包含第一电极、第二电极、位于第一电极和第二电极之间的一个或多个有机功能层,其特征在于,所述有机功能层包含如权利要求1-6任一项所述的有机化合物,或由权利要求7所述的组合物制备而成。
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