CN115322104A - 一种芴衍生物及包含它的有机发光元件 - Google Patents
一种芴衍生物及包含它的有机发光元件 Download PDFInfo
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- CN115322104A CN115322104A CN202211028804.3A CN202211028804A CN115322104A CN 115322104 A CN115322104 A CN 115322104A CN 202211028804 A CN202211028804 A CN 202211028804A CN 115322104 A CN115322104 A CN 115322104A
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- fluorene derivative
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—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
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- 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
-
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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- 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
- C07D403/14—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 three or more hetero rings
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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
- C07D405/04—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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- 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
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
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Abstract
Description
技术领域
本发明涉及有机电致发光材料技术领域,尤其涉及一种芴衍生物、有机材料、及其在有机电致发光元件中的应用。
背景技术
一般而言,有机发光现象是指在对有机物质施加电能时发出光的现象;即在阳极与阴极之间配置有机层时,如果在两个电极之间施加电压,则空穴会从阳极注入至有机层,电子会从阴极注入至有机层;当所注入的空穴和电子相遇时,会形成激子,当该激子跃迁至基态时,会发出光和热。
最近几年有机电致发光显示技术已趋于成熟,一些产品已进入市场,但在产业化过程中,仍有许多问题亟待解决。特别是用于制作元件的各种有机材料,其载流子注入和传输性能、材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等,尚有许多问题还未解决;尤其是发光元件的发光效率和使用寿命还达不到实用化要求,这大大限制了OLED技术的发展。而利用三线态发光的金属配合物磷光材料具有高的发光效率,其绿光和红光材料已经达到使用要求,但是金属配合物磷光材料要求具有高三线态能级的磷光材料或空穴材料与之匹配,因此,开发具有高三线态能级的磷光材料或空穴材料是当前OLED发展的迫切需求。
在目前的技术发展下,无论是对于荧光材料还是对于磷光材料,特别是在用于有机电致发光元件中的工作电压、效率和寿命方面和在升华期间的热稳定性方面,都还需要改进。
由此,为了克服如上所述的以往技术问题而进一步提高有机电致发光元件的特性,继续要求对于在有机电致发光元件中可用作磷光材料或空穴材料的更加稳定且有效的物质的开发。
鉴于此,特提出本发明。
发明内容
本发明的目的在于提供一种芴衍生物,该芴衍生物有效提高了材料热稳定性和输送载流子的能力,利用该芴衍生物制备的有机电致发光元件可显著降低驱动电压、提高发光效率和寿命;本发明的另一目的在于提供该芴衍生物在有机电致发光元件中的应用。
具体地,本发明提供以下技术方案:
本发明提供一种芴衍生物,其结构式如式(I)所示:
Ar1、Ar2、Ar3、Ar4各自独立地选自由氢、氘、C1-C40的烷基、C3-C40的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、取代或未取代的C2-C60杂环芳基组成的群组;
Ar5、Ar6各自独立地选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组;
m选自0~5的整数;
L1选自单键、取代或未取代的C6-C60的亚芳基、或者取代或未取代的C2-C60亚杂芳基。
本发明中,相邻基团彼此结合而形成的取代或未取代的环中,“环”是指取代或未取代的烃环、或者取代或未取代的杂环。
作为优选,所述Ar1、Ar2、Ar3、Ar4各自独立地选自由氢、C1-C40的烷基、取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂环芳基组成的群组。
作为优选,所述Ar5、Ar6各自独立地选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组。
作为优选,所述m为0、1或2。
优选地,所述芳基、杂环芳基,特别是指衍生自如下物质的基团:苯基、萘基、蒽基、苯并蒽基、菲基、芘基、基、苝基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、三聚苯基、四联苯基、芴基、螺二芴基、二氢菲基、三亚苯基、二氢芘基、四氢芘基、顺式或反式茚并芴基、顺式或反式茚并咔唑基、顺式或反式吲哚并咔唑基、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、吲哚基、异吲哚基、咔唑基、吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并[5,6]喹啉基、苯并[6,7]喹啉基、苯并[7,8]喹啉基、吩噻嗪基、吩噁嗪基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、噁唑基、苯并噁唑基、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、六氮杂苯并菲基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基、4,5,9,10-四氮杂苝基、吡嗪基、吩嗪基、吩噁嗪基、吩噻嗪基、荧红环基、萘啶基、氮杂咔唑基、苯并咔啉基、咔啉基、菲咯啉基、1,2,3-三唑基、1,2,4-三唑基、苯并三唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基、喹唑啉基、苯并噻二唑基或者衍生自这些体系的组合的基团。
进一步地,所述Ar1、Ar2、Ar3、Ar4各自独立地选自由氢、甲基、取代或未取代的苯基、取代或未取代的吡啶基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的咔唑基组成的群组。
进一步地,所述Ar5、Ar6各自独立地选自由取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的咔唑基组成的群组。
作为优选,所述L1选自单键或由以下III-1~III-15所示基团组成的群组:
其中,
Z11、Z12各自独立地选自由氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60的烷基、C2-C60的烯基、C2-C60的炔基、C1-C60的烷氧基、C3-C60的环烷烃基、C3-C60的环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组;
Z13表示取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基中的一种或多种;
y1表示1-4的整数;y2表示1-6的整数;y3表示1-3的整数;y4表示1-5的整数;
T1表示O、S、CR’R”或NAr’;
R’、R”各自独立地选自由氢、氘、C1-C60的烷基、C1-C60的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组,R’和R”可任选地接合或稠合形成另外的一个或多个取代或未取代的环,在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1-C60的烷基、C1-C60的杂烷基、C3-C60的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组;优选地,Ar’为甲基、乙基、苯基或萘基;
本发明中,“取代或未取代的”这一用语是指,被选自氢、氘、氟、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C1-C40的烷氧基、C3-C40的环烷基、C3-C40的环烯基、C6-C60的芳基、C6-C60的芳氧基、C6-C60的芳硫醚基和C2-C60的杂环芳基中的1个以上的取代基取代或未取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代或未取代。
作为优选,所述芴衍生物的结构式选自由以下C602至C760组成的群组:
其中,*-T2-*选自*-O-*、*-S-*或下述结构中的一种:
T3选自O、S或以下结构中的一种:
作为优选,所述的*-T2-*选自*-O-*、*-s-*或下述结构中的一种:
作为优选,所述的T3选自O、S或以下结构中的一种:
*-和-*表示连接键。
本发明提供了式(I)所示化合物的合成路线,如下所示:
其中,X1、X2表示I、Br、Cl或OTf;其它所用符号如上文中所定义。
合成式(I)所示化合物的原料可通过商业途径购买而得,此方法原理、操作过程、常规后处理、过柱纯化、重结晶提纯等手段是本领域合成人员所熟知的,完全可以实现合成过程,得到目标产物。
具体地,式(I)的化合物是由X1、X2取代的苊、苊烯或荧蒽经过取代反应、缩合反应、SUZUKI偶联等反应制备而成的。中间体Ar1(L2)nB(OH)2、Ar2Ar3N-(L1)mB(OH)2、Ar4Ar5N-(L3)xB(OH)2或Ar2Ar3NH、Ar4Ar5NH通过钯催化或碱催化偶联反应制备。
作为可用于钯催化偶联反应的钯催化剂可选自:Pd(P-tBu3)2、Pd(PPh3)4、Pd2(dba)3、Pd2(dba)3CHCl3、PdCl2(PPh3)2、PdCl2(CH3CN)2、Pd(OAc)2、Pd(acac)2、Pd/C、PdCl2、[Pd(allyl)Cl]2等任意一种,或使用两种或更多种的混合物。
此外,钯催化的偶联反应或碱催化的偶联反应使用的碱可选自:叔丁醇钠、叔丁醇钾、氢化钠、氢化锂、叔戊醇钠、乙醇钠、甲醇钠、碳酸钠、碳酸钾、碳酸铯、锂、氢化钾、三乙胺、氟化铯等,以及其中一种或两种或更多种的混合物。
偶联反应可以在有机溶剂中进行,其中有机溶剂可选自:乙醚、四氢呋喃、2-甲基四氢呋喃、1,4-二氧六环、乙二醇乙醚、乙二醇二乙醚、乙二醇甲醚、二甘醇二乙醚、或苯甲醚等醚类溶剂;苯、甲苯、二甲苯等芳烃类剂;氯苯、二氯苯、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、二甲基亚砜、环丁砜等,可以使用一种或两种以上的混合物。
本发明还提供一种有机电致发光材料,其原料包括以上所述的芴衍生物;包括本发明的芴衍生物的有机电致发光材料具有载流子传输的能力或光取出能力。
作为优选,所述有机电致发光材料为空穴注入层材料、空穴传输层材料、空穴阻挡层材料、发光层材料、电子传输层材料、电子注入层材料、封盖层材料或电子阻挡层材料。
本发明还提供一种有机电致发光元件,其包括:第一电极、第二电极、封盖层和置于所述第一电极、所述第二电极之间的一层以上的有机层;所述有机层、光取出层中的至少一层包括以上所述的芴衍生物。
所述有机电致发光元件包含第一电极、第二电极、封盖层和至少一个发光层。除了这些层之外,它还可以包含其它的层,例如在每种情况下,包含一个或多个空穴注入层、空穴传输层、功能层,同时具备空穴注入和空穴传输功能、电子传输层、电子注入层、激子阻挡层,包括电子阻挡层和空穴阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而,应当指出,这些层中的每个并非必须都存在。此处所述有机电致发光元件可包含一个发光层,或者它可包含多个发光层。即,将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系,其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层,则根据本发明,这些层中的至少一个层包含本发明的化合物。
进一步地,根据本发明的有机电致发光元件不包含单独的空穴注入层和/或空穴传输层和/或空穴阻挡层和/或电子传输层,即发光层与空穴注入层或阳极直接相邻,和/或发光层与电子传输层或电子注入层或阴极直接相邻。
在根据本发明的有机电致发光元件的其它层中,特别是在空穴传输层和发光层中以及在光取出层中,所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。
此外优选如下的有机电致发光元件,可以借助于升华方法施加一个或多个层,其中在真空升华装置中在低于10-5Pa、优选低于10-6Pa的初压下通过气相沉积来施加所述材料。然而,所述初压还可能甚至更低,例如低于10-7Pa。
同样优选如下的有机电致发光元件,也可以借助于有机气相沉积方法或借助于载气升华来施加一个或多个层,其中,在10-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸气喷印方法,其中所述材料通过喷嘴直接施加,并且因此是结构化的。
此外优选如下的有机电致发光元件,从溶液中,例如通过旋涂,或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷,来产生一个或多个层。可溶性化合物,例如通过适当的取代式(I)所示的化合物获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法,其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。
这些方法是本领域普通技术人员通常已知的,并且他们可以在不付出创造性劳动的情况下将其应用于包含根据本发明的化合物的有机电致发光元件。
因此,本发明还涉及制造根据本发明的有机电致发光元件的方法,包括借助于升华方法来施加至少一个层,和/或借助于有机气相沉积方法或借助于载气升华来施加至少一个层,和/或从溶液中通过旋涂或借助于印刷方法来施加至少一个层。
此外,本发明涉及包含至少一种上文指出的本发明的化合物。如上文关于有机电致发光元件指出的相同优选情况适用于所述本发明的化合物。特别是,所述化合物此外还可优选包含其它化合物。从液相处理本发明的化合物,例如通过旋涂或通过印刷方法进行处理,需要处理本发明的化合物的制剂,这些制剂可以例如是溶液、分散体或乳液。出于这个目的、可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯、苯甲醚、邻二甲苯、间二甲苯或对二甲苯、苯甲酸甲酯、均三甲苯、萘满、邻二甲氧基苯、四氢呋喃、甲基四氢呋喃、四氢吡喃、氯苯、二噁烷、苯氧基甲苯,特别是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-吡咯烷酮、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、异丙苯、环己醇、环己酮、环己基苯、十氢化萘、十二烷基苯、苯甲酸乙酯、茚满、苯甲酸甲酯、1-甲基吡咯烷酮、对甲基异丙基苯、苯乙醚、1,4-二异丙基苯、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、二乙二醇单丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-异丙基萘、戊苯、己苯、庚苯、辛苯、1,1-双(3,4-二甲基苯基)乙烷,或这些溶剂的混合物。
本发明还提供一种有机电致发光元件的应用,所述有机电致发光元件使用于从如下装置中选择的任意一种装置:
平板显示装置;柔性显示装置;单色或白色的平板照明用装置;或单色或白色的柔性照明用装置。
本发明所取得的有益效果:
本发明提供的式(I)所示的芴衍生物,增大了芴平面的共轭能力,具有高的玻璃化转变温度和三线态能级,提高了材料热稳定性和输送载流子的能力,且分子在真空条件下易形成均匀的薄膜。将该芴衍生物应用在有机电致发光元件中,可显著降低驱动电压、提高发光效率和寿命。
附图说明
图1展示有机发光装置100示意图。图示不一定按比例绘制。装置100可包含衬底101、阳极102、空穴注入层103、空穴传输层104、电子阻挡层105、发光层106、空穴阻挡层107、电子传输层108、电子注入层109、阴极110以及封盖层(CPL)111。装置100可通过依序沉积所描述的层来制造。
图2展示两个发光层的有机发光装置200示意图。所述装置包含衬底201、阳极202、空穴注入层203、空穴传输层204、第一发光层205、电子传输层206、电荷产生层207、空穴注入层208、空穴传输层209、第二发光层210、电子传输层211、电子注入层212以及阴极213。可通过依序沉积所描述的层来制备装置200。因为最常见的OLED装置具有一个发光层,而装置200具有第一发光层和第二发光层,第一发光层和第二发光层的发光峰形可以是重叠的或交叉重叠的或非重叠的。在装置200的对应层中,可使用与关于装置100所描述的材料类似的材料。图2提供可如何从装置100的结构增加一些层的一个实例。
具体实施方式
以下实施例用于说明本发明,但不用来限制本发明的范围。
在本发明的描述中,除非另有说明,“多个”的含义是两个或两个以上;术语“上”、“下”等指示的方位或位置关系为基于附图所示的方位或位置关系,仅是为了便于描述本发明和简化描述,而不是指示或暗示所指的装置或元件必须具有特定的方位、以特定的方位构造和操作,因此不能理解为对本发明的限制。
以下实施例中所使用的实验方法如无特殊说明,均为常规方法。以下实施例中所用的实验原料和相关设备等,如无特殊说明,均可从商业途径得到,所述百分比如无特殊说明,均为质量百分比。
另外,如无特殊说明,本发明所记载的任何范围包括端值以及端值之间的任何数值以及端值或者端值之间的任意数值所构成的任意子范围。
下述实施例对OLED材料及元件进行性能测试的测试仪器及方法如下:
OLED元件性能检测条件:
亮度和色度坐标:使用光谱扫描仪PhotoResearch PR-715测试;
电流密度和起亮电压:使用数字源表Keithley 2420测试;
功率效率:使用NEWPORT 1931-C测试。
实施例1
化合物C650的制备方法,包括如下步骤:
第一步:中间体Int-1的制备
20.0mmol的2-溴-9,9-螺二芴、10.0mmol的邻碘苯乙酮、20.0mmol的碳酸银、0.1mmol的氯化钯、0.2mmol的三(对甲苯基)膦、10.0mmol的碳酸钾和10mL的甲苯、10mL的水混合,通入氮气保护,升温至100℃搅拌反应12小时,降到室温,加入100mL的饱和氯化铵水溶液,分出有机相,水相用乙酸乙酯萃取,收集有机相,干燥,减压浓缩干,过硅胶柱分离纯化,得化合物Int-1,白色固体,收率:65%。
第二步:化合物Int-2的制备
在氮气保护下,20.0mmol的中间体Int-1溶于40mL干燥的THF中,降温至0℃,滴加入22.0mmol的1M甲基溴化镁THF溶液,升至室温搅拌反应1小时,加入20mL的2N稀盐酸水溶液,分出有机相,水相用乙酸乙酯萃取,收集有机相,干燥,减压浓缩干,过硅胶柱分离纯化,得化合物Int-2,黄色固体,收率:85%。
第三步:化合物Int-3的制备
在氮气保护下,20.0mmol的中间体Int-2溶于60mL干燥的二氯甲烷中,降温至0℃,滴加入30.0mmol的三氟化硼乙醚溶液,升至室温搅拌反应12小时,加入20mL的水,分出有机相,水相用二氯甲烷萃取,收集有机相用5%的氢氧化钠水溶液洗,水洗,有机相干燥,减压浓缩干,过硅胶柱分离纯化,得化合物Int-3,白色固体,收率:87%。
第四步:化合物C650的制备
在氮气保护下,20.0mmol的中间体Int-3溶于60mL干燥的甲苯中,加入22.0mmol的芳胺、30.0mmol的叔丁醇钠、0.2mmol的Pd2(dba)3和0.4mmol的xantPhos,升温至100℃搅拌反应12小时,降到室温,加入50mL的水,分出有机相,水相用甲苯萃取,有机相合并干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得化合物C650;
T2=O,白色固体,收率:79%,MS(MALDI-TOF):m/z=766.3118[M+H]+;1HNMR(δ、CDCl3):8.02(1H,s);7.92~7.86(4H,m);7.63~7.61(1H,d);7.55~7.49(5H,m);7.46~7.33(13H,m);7.30~7.23(6H,m);7.17~7.14(2H,m);7.03~6.98(1H,m);1.67(6H,s)。
T2=S,白色固体,收率:78%,MS(MALDI-TOF):m/z=782.2895[M+H]+;1HNMR(δ、CDCl3):8.42(1H,s);8.23(1H,s);8.01~7.98(1H,d);7.92~7.81(4H,m);7.74~7.68(3H,m);7.62(1H,s);7.56~7.44(11H,m);7.41~7.36(3H,m);7.31~7.24(6H,m);7.19~7.14(2H,m);1.67(6H,s)。
T2=CMe2,白色固体,收率:76%,MS(MALDI-TOF):m/z=792.3644[M+H]+;1HNMR(δ、CDCl3):8.25(1H,s);7.92~7.86(5H,m);7.74~7.69(3H,m);7.67(1H,s);7.55~7.49(4H,m);7.46~7.26(16H,m);7.18~7.12(3H,m);1.68~1.67(12H,d)。
T2=NPh,白色固体,收率:77%,MS(MALDI-TOF):m/z=841.3598[M+H]+;1HNMR(δ、CDCl3):8.37~8.35(1H,d);8.25~8.19(2H,m);7.92~7.85(3H,m);7.74~7.68(3H,m);7.61~7.56(5H,m);7.54~7.36(14H,m);7.34~7.26(6H,m);7.20~7.14(4H,m);1.67(6H,s)。
参照上述类似的合成方法,制备以下表1所示化合物:
表1
其中,*-T2-*、*-T3-*选自*-O-*、*-S-*或下述结构中的一种:
实施例2
化合物C671的制备方法,包括如下步骤:
第一步:中间体Int-4的制备
参照实施例1的合成方法,仅将实施例1第一步中的2-溴-9,9-螺二芴替换为2-溴-9,9-二甲基芴,将邻碘苯乙酮替换为(邻苯基苯甲酰基)-2-碘苯,黄色固体,收率:57%。
第二步:化合物Int-5的制备
在氮气保护下,20.0mmol的中间体Int-4溶于20mL的三氟甲磺酸中,升温至回流搅拌反应12小时,降到室温,加入100mL的冰水溶液,过滤,滤饼用水洗,黄色固体用硅胶柱分离纯化,得化合物Int-5,白色固体,收率:76%。
第三步:化合物C671的制备
在氮气保护下,22.0mmol的中间体Int-5溶于50mL干燥的甲苯中,加入20.0mmol的二联苯基胺、30.0mmol的叔丁醇钠、0.2mmol的Pd2(dba)3和0.4mmol的XantPhos,升温至100℃搅拌反应12小时,降到室温,加入50mL的水,分出有机相,水相用甲苯萃取,有机相合并干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得化合物C671,白色固体,收率:83%,MS(MALDI-TOF):m/z=752.3325[M+H]+;1HNMR(δ、CDCl3):8.23(1H,s);8.11(1H,s);7.92~7.86(3H,m);7.74~7.69(3H,m);7.56~7.49(6H,m);7.46~7.31(14H,m);7.28~7.23(5H,m);7.16~7.12(1H,m);7.10~7.08(1H,m);1.67(6H,s)。
参照上述类似的合成方法,制备以下表2所示化合物:
表2
其中,*-T2-*、*-T3-*选自*-O-*、*-S-*或下述结构中的一种:
实施例3
化合物C739的制备:
在氮气保护下,20.0mmol的中间体Int-3溶于40mL的甲苯中,加入22.0mmol的4-(二联苯基胺基)苯硼酸频哪醇酯、60.0mmol的碳酸钠、0.01mmol的Pd0132和20mL的乙醇、20mL的水,升温至回流搅拌反应12小时,降到室温,加入50mL的水,分出有机相,水相用甲苯萃取,有机相合并干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得化合物C739,白色固体,收率:89%,MS(MALDI-TOF):m/z=828.3644[M+H]+;1HNMR(δ、CDCl3):8.22(1H,s);8.10(1H,s);8.01(1H,s);7.91~7.86(3H,m);7.74~7.69(3H,m);7.56~7.47(8H,m);7.44~7.30(15H,m);7.28~7.19(5H,m);7.16~7.12(1H,m);7.10~7.07(1H,m);1.67(6H,s)。
参照上述类似的合成方法,制备以下表3所示化合物:
表3
其中,*-T2-*、*-T3-*选自*-O-*、*-S-*或下述结构中的一种:
实施例4
一种有机电致发光元件200,其结构如图2所示,包括基板101、设于基板101上的阳极层102、设于阳极层102上的空穴注入层103、设于空穴注入层103上的空穴传输层104、设于空穴传输层104上的电子阻挡层105、设于电子阻挡层105上的发光层106、设于发光层106上的电子传输层107、设于电子传输层107上的电子注入层108、设于电子注入层108上的阴极层109,以及设于阴极层之上的CPL层110,其制备方法包括如下步骤:
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟,在去离子水中冲洗,在丙酮/乙醇混合溶剂中超声30分钟,在洁净的环境下烘烤至完全干燥,用紫外光清洗机照射10分钟,并用低能阳离子束轰击表面。
2)把上述处理好的ITO玻璃基片置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述ITO膜上蒸镀金属银作为阳极层,蒸镀膜厚为蒸镀化合物HI01和HI102作为空穴注入层,其中HI102为HI01质量的3%,蒸镀膜厚为
实施例4中使用的化合物HI01、H1102、HTM、PHT、GD018、ET010和LiQ的结构如下:
实施例5
一种有机电致发光元件100,其结构如图1所示,包括基板101、设于基板101上的阳极层102、设于阳极层102上的空穴注入层103、设于空穴注入层103上的空穴传输层104、设于空穴传输层104上的电子阻挡层105、设于电子阻挡层105上的发光层106、设于发光层106上的空穴阻挡层107、设于空穴阻挡层107上的电子传输层108、设于电子传输层108上的电子注入层109、设于电子注入层109上的阴极层110,以及设于阴极层110之上的CPL111。
对比例1
按照与实施例4相同的步骤,将步骤4)中的式(I)所示的化合物替换为B-1,得到对比元件1;B-1结构式如下:
对比例2
按照与实施例4相同的步骤,将步骤4)中的式(I)所示的化合物替换为B-2,得到对比元件2;B-2结构式如下:
对比例3
按照与实施例2相同的步骤,将步骤4)中的式(I)所示的化合物替换为B-3,得到对比元件3;B-3结构式如下:
所得元件的性能检测数据以对比元件1为基准进行归一化处理,其结果列于表4中,其中驱动电压、发光效率和半峰宽(FWHM)是在元件的电流密度为10mA/cm2条件下得出,元件的LT95%寿命是在电流密度为50mA/cm2的起始条件下测得。
表4各元件性能检测结果
表中,Me为甲基;Ph为苯基;PhPh为联苯基;Nap为萘基;FR为9,9-芴基。
由表4可知,本发明的芴衍生物作为电子阻挡材料制备成的发光元件同样在10mA/cm2条件下,驱动电压相较B-1、B-2、B-3降低,发光效率和LT95%寿命性能提高明显,发光效率最高达到对比元件的1.3倍之多,尤其是LT95%寿命最高超过对比元件3倍,说明本发明的化合物母核稳定性比提高,是性能优异的电子阻挡层材料。
本发明的芴衍生物与对比例的化合物B-1相比,区别在于B-1为螺二芴的正交结构,与芳胺基团平面形成90度夹角,空间位阻很大,而本发明的芴衍生物芳胺基团与芴在同一平面,位阻小,其在分子成膜及电荷的传输上性能均较优异,元件内部的电荷传输更加平衡,因此,元件性能提高,本发明的化合物在发光元件的性能表现上更加优异。
本发明的芴衍生物与对比例的化合物B-2相比,区别在于B-2为双芳胺结构,具有较深的HOMO能级,造成元件内的激子传输不平衡和较大的载流子注入势垒,这种不平衡使元件驱动电压升高,效率降低。而本发明的芴衍生物为一个芳胺基团,空间位阻小,降低了载流子注入势垒,其在分子成膜及电荷的传输上性能均较优异,元件内部的激子传输更加平衡,因此,元件性能提高,本发明的化合物在发光元件的性能表现上更加优异。
本发明的芴衍生物与对比例的化合物B-3相比,区别在于B-3的平面共轭能力弱,空间位阻大。而本发明的芴衍生物的芳胺基团在芴的4位,平面共轭增强,芳胺基团阻挡芴平面使螺二芴的正交结构夹角变小,因此其在分子成膜及电荷的传输上性能优异,元件内部的激子传输更加平衡,因此,元件性能提高,本发明的化合物在发光元件的性能表现上更加优异。
虽然,上文中已经用一般性说明及具体实施方案对本发明作了详尽的描述,但在本发明基础上,可以对之作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。
Claims (10)
2.根据权利要求1所述的芴衍生物,其特征在于,所述Ar1、Ar2、Ar3、Ar4各自独立地选自由氢、C1-C40的烷基、取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂环芳基组成的群组;
Ar5、Ar6各自独立地选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组;
m为0、1或2。
3.根据权利要求1所述的芴衍生物,其特征在于,所述Ar1、Ar2、Ar3、Ar4各自独立地选自由氢、甲基、取代或未取代的苯基、取代或未取代的吡啶基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的咔唑基组成的群组;
Ar5、Ar6各自独立地选自由取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的咔唑基组成的群组。
4.根据权利要求1-3任一项所述的芴衍生物,其特征在于,所述L1选自单键或由以下III-1~III-15所示基团组成的群组:
其中,
Z11、Z12各自独立地选自由氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60的烷基、C2-C60的烯基、C2-C60的炔基、C1-C60的烷氧基、C3-C60的环烷烃基、C3-C60的环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组;
Z13表示取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基中的一种或多种;
y1表示1-4的整数;y2表示1-6的整数;y3表示1-3的整数;y4表示1-5的整数;
T1表示O、S、CR’R”或NAr’;
R’、R”各自独立地选自由氢、氘、C1-C60的烷基、C1-C60的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组,R’和R”可任选地接合或稠合形成另外的一个或多个取代或未取代的环,在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1-C60的烷基、C1-C60的杂烷基、C3-C60的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组;优选地,Ar’为甲基、乙基、苯基或萘基;
7.一种有机电致发光材料,其特征在于,其原料包括权利要求1-6任一项所述的芴衍生物。
8.一种有机电致发光元件,其特征在于,其包括:第一电极、第二电极、封盖层和置于所述第一电极、所述第二电极之间的一层以上的有机层;所述有机层、封盖层中的至少一层包括权利要求1-6任一项所述的芴衍生物。
9.根据权利要求8所述的有机电致发光元件,其特征在于,所述有机层包括如下层中的至少一层:空穴注入层、空穴传输层、同时具备空穴注入和空穴传输功能的功能层、发光层、电子传输层、电子注入层以及电子阻挡层;所述各个层中选择的一个以上的层通过沉积工艺或溶液工艺而形成。
10.如权利要求8或9所述的有机电致发光元件,其特征在于,所述有机电致发光元件使用于从如下装置中选择的任意一种装置:
平板显示装置;
柔性显示装置;
单色或白色的平板照明用装置;或
单色或白色的柔性照明用装置。
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