CN117263947A - 一种杂环化合物及其应用 - Google Patents
一种杂环化合物及其应用 Download PDFInfo
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- CN117263947A CN117263947A CN202311193906.5A CN202311193906A CN117263947A CN 117263947 A CN117263947 A CN 117263947A CN 202311193906 A CN202311193906 A CN 202311193906A CN 117263947 A CN117263947 A CN 117263947A
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- heterocyclic compound
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- 239000000463 material Substances 0.000 claims abstract description 28
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 155
- -1 aryl phosphine Chemical compound 0.000 claims description 143
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 238000002347 injection Methods 0.000 claims description 30
- 239000007924 injection Substances 0.000 claims description 30
- 230000000903 blocking effect Effects 0.000 claims description 19
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 12
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
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- 239000001257 hydrogen Substances 0.000 claims description 9
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- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 8
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- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
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- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 3
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 3
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- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 2
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 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
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
本发明涉及有机电致发光材料技术领域,尤其涉及一种杂环化合物及其应用。所述杂环化合物的结构式如式(I)所示;本发明提供的式(I)所示化合物,具有两个咪唑结构。将该化合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;
Description
技术领域
本发明涉及有机电致发光材料技术领域,尤其涉及一种杂环化合物及其在有机发光元件中的应用。
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;尤其是应用于电子注入层和传输层的物质,作为与电子传输材料有关的最早报告,可以举出恶二唑衍生物,三唑衍生物、菲咯啉衍生物和在专利CN107573328A、CN107556310A、CN113801066A、CN113429395A、CN113429348A、CN114560872A等记载的咪唑基的代表性电子传输层用物质,其结构中含有N-苯基苯并咪唑基,就功能而言,不仅具有传输电子的能力,而且具有阻断从发光层跨越来的空穴的功能,但在应用于实际元件时存在热稳定性低的问题。
由此,为了克服如上所述的技术问题,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电子注入和传输用物质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杂环化合物,该杂环化合物可提高材料热稳定性和输送载流子的能力,利用该杂环化合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化合物的应用。
具体地,本发明提供以下技术方案:
本发明提供一种杂环化合物,其结构式如式(I)所示:
其中,
L1、L2各自独立地选自由单键、取代或未取代的C6-C60亚芳基、或者取代或未取代的C2-C60亚杂芳基组成的群组;
X1、X2、X3、X4、X5、X6各自独立地表示CR1或N;
G表示O、S、SO、SO2、Se、CR2R3、SiR2R3或NAr3;
R1、R2、R3各自独立地选自由氢、氘、氟、腈基、取代或未取代的C1-C40烷基、取代或未取代的C1-C40烷氧基、取代或未取代的C2-C40烯基、取代或未取代的C1-C40烷硫基、取代或未取代的C1-C40烷氧基、取代或未取代的C3-C40环烷基、取代或未取代的C1-C40烷基亚砜基、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芳硫基、取代或未取代的C6-C60芳基亚砜基、取代或未取代的C3-C40甲硅烷基、取代或未取代的硼基、取代或未取代的胺基、取代或未取代的芳基膦基、取代或未取代的氧化膦基、或者取代或未取代的C2-C60杂环芳基组成的群组;任意相邻的两个或多个取代基可以任意的接合或稠合形成取代或未取代的环;
Ar1、Ar2、Ar3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。
本发明中所述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。缩合环是指缩合脂肪环、缩合芳香环、缩合脂肪杂环、缩合芳香杂环或它们组合而成的形态。
根据本发明的杂环化合物由上述化学式(I)所示,其中,包含苯并呋喃并喹啉、苯并呋喃并菲罗啉、苯并噻吩并喹啉、苯并噻吩并菲罗啉等杂环通过单键、亚芳基、亚杂芳基的L1、L2结合而形成基本骨架。本发明的式(I)所示的化合物与以往已知的苯并呋喃、苯并噻吩并喹啉或并菲罗啉等杂环结构相比,不仅在电化学上稳定、电子移动性优异,而且玻璃化转变温度高且热稳定性优异。由此,本发明的杂环化合物的电子传输能力和发光特性优异,因此可用作有机电致发光元件的有机物层的空穴注入层、空穴传输层、发光层、电子传输层和空穴阻挡层中的任意一层的材料。优选可用作发光层、电子传输层和在电子传输层上时一步层叠的电子传输辅助层中的任意一层的材料,更优选可用作电子传输层或电子传输辅助层的材料。
具体而言,本发明的化合物式(I)所示的化合物通过包含喹啉或菲罗啉的杂环化合物,从而与吸电子基团能力弱的二苯并呋喃、二苯并噻吩等杂环相比,具有更强的电子传输能力,能够显示相对高的发光效率和高玻璃化转变温度。由此,在将本发明的式(I)所示杂环化合物用于有机电致发光元件的情况下,不仅能够具有优异的热稳定性、载流子传输能力,电子传输能力和发光能力,而且能够降低元件的驱动电压、提高效率和寿命等,并且作为最新电子传输层材料,能够因高三重态能级而显示出三重态-三重态融合效果所引起的优异的效率上升。
此外,本发明的式(I)所示的杂环化合物通过在基本骨架中导入多种取代基R1、Ar1、Ar2,根据取代基的种类来调节HOMO和LUMO能级,从而能够具有宽的带隙,在使用这样的化合物的有机电致发光元件中能够显示高电子传输性。
此外,本发明的式(I)所示的杂环化合物通过引入至上述基本骨架的多种取代基L1、L2和Ar1、Ar2,尤其芳基和/或杂芳基,化合物的分子量显著增加,从而玻璃化转变温度提高,由此较以往的发光材料,例如菲啶,具有更高的热稳定性。因此,能够使包含根据本发明的化合物的有机电致发光元件的性能和寿命特性大大提高。如此性能和寿命特性提高了的有机电致发光元件最终能够使全彩有机发光面板的性能最大化。
本发明的式(I)所示的杂环化合物,作为优选,所述杂环化合物选自由以下结构组成的群组:
其中,所用符号的含义与上述的定义相同。
本发明意义上的芳基含有6~60个碳原子,杂芳基含有2~60个碳原子和至少一个杂原子,其条件是碳原子和杂原子的总和至少是5;所述杂原子优选选自N、O或S。此时,杂芳基的两个以上的环可以彼此简单附着或以缩合的形态附着,进一步地,也可以包含与芳基缩合的形态。作为这样的杂芳基的非限制性例子,可以举出诸如吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基之类的六元单环;诸如吩噁噻基、吲哚嗪基、吲哚基、嘌呤基、喹啉基、苯并噻唑基、咔唑基之类的多环;以及2-呋喃基、N-咪唑基、2-异噁唑基、2-吡啶基、2-嘧啶基等。
进一步地,所述芳基、杂芳基或杂环芳基优选选自由苯基、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、吲哚并咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、苯并咔唑基、二苯并咔唑基、氮杂二苯并[g,ij]萘并[2,1,8-cde]薁、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、苯并噻二唑基组成的群组或者衍生自这些体系的组合的基团。
进一步地,所述R1、R2、R3各自独立地选自由氢、氘、甲基、取代或未取代的苯基、取代或未取代的芴基组成的群组。
进一步地,所述G选自O或S。
进一步地,所述X1为N和/或X1~X6为CR1。
进一步地,所述Ar1、Ar2、Ar3各自独立地选自由取代或未取代的以下基团组成的群组: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、吲哚并咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、苯并咔唑基、二苯并咔唑基、氮杂二苯并[g,ij]萘并[2,1,8-cde]薁、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。
根据本发明的实施例,所述R1选自氢、氘、氟或腈基。
进一步地,所述杂芳基或杂环芳基选自由以下II-1~II-17所示基团组成的群组:
其中,
Z1、Z2各自独立地选自由氢、氘、卤素、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烷基、C2~C40烯基、C2~C40炔基、C1~C40烷氧基、C3~C40环烷烃基、C3~C40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C5~C60杂环芳基组成的群组;
x1表示1-4的整数;x2表示1-3的整数;x3表示1或2;x4表示1-6的整数;x5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~C40的烷基、C1~C40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C5~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~C40的烷基、C1~C40的杂烷基、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、或者取代或未取代的C5~C60杂环芳基组成的群组;优选地,Ar’为甲基、乙基、苯基、联苯基或萘基;
表示键合的位置。
进一步地,所述Ar1、Ar2、Ar3各自独立地选自由取代或未取代的以下基团组成的群组: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、吲哚并咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、苯并咔唑基、二苯并咔唑基、氮杂二苯并[g,ij]萘并[2,1,8-cde]薁、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。
本发明的式(I)所示的杂环化合物中,L1、L2为将上述含有苯并呋喃并喹啉、苯并呋喃并菲罗啉、苯并噻吩并喹啉、苯并噻吩并菲罗啉的杂环骨架与上述Ar1、Ar2连接的官能团,可以选自由单键、C6-C60的亚芳基和C2-C60杂亚芳基组所的组。此时,作为优选,所述L1、L2各自独立地选自单键或由以下III-1~III-23所示基团组成的群组:
其中,虚线代表基团的连接位点,此时,上述式III-1~III-23所示基团的结合位置并非限制,邻、间、对均可。上述的L1、L2可各自独立地被选自由氘、卤原子、腈基、C1-C40烷基、C6-C60芳基和C2-C60杂环芳基组成的群组中的一种以上取代,此时,当取代基为多个时,优选多个取代基彼此相同或不同。
本发明中,“取代或未取代的”这一用语是指,被选自氢、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-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷基、C3-C40环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60芳硫醚基和C2-C60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。
对于本发明意义上的烷基含有1~40个碳原子,并且其中单独的氢原子或-CH2-基团还可被取代的直链烷基或带有支链的烷基;烯基或炔基至少含有两个碳原子,作为非限制性的例子,烷基、烯基或炔基优选被认为是指如下基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。
烷氧基优选具有1~40个碳原子的烷氧基被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。
杂烷基优选具有1~40个碳原子的烷基,是指其中单独的氢原子或-CH2-基团被氧、硫、卤素原子取代的基团,作为非限制性的例子,烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基,特别是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
一般来说,根据本发明的环烷基、环烯基可以为环丙基、环丁基、环戊基、环己基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基,其中一个或多个-CH2-基团可被上述基团代替;此外,一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
本发明中使用的杂环烷基是指原子核数从3至40的非芳香族烃去除一个氢原子而得到的一价官能团。此时,环中一个以上的碳、优选为1至3个碳被诸如N、O或S之类的杂原子取代。作为其非限制性例子,有四氢呋喃、四氢噻吩、吗啉、哌嗪等。
本发明中使用的稠环芳基是指组合了两个以上的环的碳原子数从6至60的芳香族烃去除一个氢原子而得到的一价官能团。此时,两个以上的环可以彼此单纯附着或者以缩合的形态附着。作为其非限制性例子,例如有菲基、蒽基、荧蒽基、芘基、三亚苯基、苝基、基等。
本发明中使用的芳胺基是指被碳原子数从6至60的芳基取代的胺,作为芳胺基的非限制性例子,有二苯胺基、N-苯基-1-萘胺基、N-(1-萘基)-2-萘胺基等。杂芳胺基是指被碳原子数6至60的芳基和被碳原子数2至60的杂芳基取代的胺,作为杂芳胺基的非限制性例子,有N-苯基吡啶-3-胺基、N-([1,1'-联苯]-4-基)二苯并[b,d]呋喃-2-胺基、N-([1,1'-联苯]-4-基)-9,9-二甲基-9H-芴-2-胺基等。
本发明中使用的烷氧基是指RO-所表示的一价官能团,所述R是碳原子数从1至40个的烷基,可以包含直链、支链或环结构。作为这样的烷氧基的非限制性例子,可以举出甲氧基、乙氧基、正丙氧基、1-丙氧基、叔丁氧基、正丁氧基、戊氧基、环戊氧基、环己氧基等。
本发明中使用的芳氧基是指R'O-所表示的一价官能团,上述R'是碳原子数从6至60的芳基。作为这样的芳氧基的非限制性例子,有苯氧基、萘氧基、联苯氧基等。
本发明中使用的烷基硅基是指被碳原子数1至40的烷基取代的硅烷基,构成烷基硅基的碳原子数至少是3,作为烷基硅基的非限制性例子,有三甲基硅基、三乙基硅基等。芳基甲硅烷基是指被碳原子数从6至60的芳基取代的甲硅烷基。
本发明中使用的芳基磷基是指被碳原子数6至60的芳基取代的二芳基磷基,作为芳基磷基的非限制性例子,有二苯基磷基、二(4-三甲基硅基苯)磷基等。芳基氧磷基是二芳基磷基的磷原子被氧化至最高价态。
本发明中使用的芳基硼基是指被碳原子数6至60的芳基取代的二芳基硼基,作为芳基硼基的非限制性例子,有二苯基硼基、二(2,4,6-三甲基苯)硼基等。烷基硼基是指被碳原子数1至40的烷基取代的二烷基硼基,作为烷基硼基的非限制性例子,有二叔丁基硼基、二异丁基硼基等。
作为优选,所述杂环化合物选自如下式J544-J660所示的化合物:
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其中,T选自O、S、SO、Se、CMe2、CPh2、NPh、NPhPh;
X选自O或S;
Me表示甲基、Ph表示苯基、PhPh表示联苯基。
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杂环化合物;包括本发明的杂环化合物的有机电致发光材料具有载流子传输的能力。
本发明还提供以上所述的杂环化合物在制备有机电致发光元件中的应用。
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;所述有机层或封盖层中的至少一层的材料包括以上所述的杂环化合物。
所述有机电致发光元件包含阴极、阳极和至少一个发光层。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、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/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装置可包含一个发光层,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杂环化合物。
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,即发光层与电子阻挡层或空穴传输层或阳极直接相邻,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,特别是在空穴注入和空穴传输层中以及在电子注入和电子传输层中,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,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,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,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杂环化合物。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,所述杂环化合物之外还可优选包含其它化合物。从液相处理本发明的杂环化合物,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。
作为优选,所述有机层包括空穴注入层、空穴传输层、空穴阻挡层、发光层、电子传输层、电子注入层或电子阻挡层。
本发明同时提供一种消费型产品,其包括以上所述的有机电致发光元件。本发明中所述的消费型产品可以是以下装置中的一种:平板显示器、计算机监视器、医疗监视器、电视机、告示牌、用于内部或外部照明和/或发信号的灯、平视显示器、全透明或部分透明的显示器、柔性显示器、激光打印机、电话、蜂窝电话、平板电脑、平板手机、个人数字助理(PDA)、可佩戴装置、膝上型计算机、数码相机、摄像机、取景器、对角线小于2英寸的微型显示器、3-D显示器、虚拟现实或增强现实显示器、交通工具、包含多个平铺在一起的显示器的视频墙、剧院或体育馆屏幕、光疗装置和指示牌。
另外,如无特殊说明,本发明中所用原料均可通过市售商购获得,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。
本发明所取得的有益效果:
本发明提供的式(I)所示杂环化合物由于电子移动性、热稳定性和发光特性优异,而能够应用于有机电致发光元件的有机物层。特别是,在将本发明的式(I)所示杂环化合物用于电子传输层和电子传输辅助层的情况下,能够制造与以往的电子传输材料相比具有更低驱动电压、更高效率以及更长寿命的有机电致发光元件,进而,还能够制造性能和寿命提高的全彩显示器面板。
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可包含基板101、阳极102、空穴注入层103、空穴传输层104、电子阻挡层105、有机发光层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。所述装置包含基板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。
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J569的制备方法,以X=O为例,包括如下步骤:
第一步:中间体Int-1的制备
参照文献:Org.Lett.,2021,23,9526-9532公开的合成方法,在氮气保护下,20.0mmol的sub-1、24.0mmol的sub-2溶于50mL的1,2-二氯乙烷,再加入40.0mmol的三氟甲烷磺酸,升温至90℃,搅拌反应10小时,冷却到室温,减压浓缩干燥,用硅胶柱分离纯化,得到化合物Int-1,白色固体,收率:66%。
第二步:中间体Int-2的制备
在氮气保护下,20.0mmol上步制备的Int-1、80.0mmol的无水碳酸钾和60mL的DMF混合,升温至125℃,搅拌反应5小时,冷却到室温,将反应液倒入150mL冰水中,过滤,滤饼用水洗,甲醇重结晶,得到化合物Int-2,白色固体,收率87%。
第三步:中间体Int-3的制备
20.0mmol上步制备的Int-2溶于100mL的二甲苯中,加入2.0g的10%钯/碳,升温至回流搅拌反应15小时,降至室温,过滤,滤饼用二氯甲烷洗,滤液减压浓缩干燥,硅胶柱分离纯化,得到化合物Int-3,白色固体,收率92%。
第四步:中间体Int-4的制备
20.0mmol上步制备的Int-3溶于50mL的二氯甲烷,分批加入22.0mmol的N-溴代琥珀酰亚胺,于室温搅拌反应2小时,加入50mL水,分出有机相用水洗三次,有机相干燥,过滤,滤液减压浓缩干燥,得到化合物Int-4,黄色固体,收率100%。
第五步:中间体Int-5的制备
在氮气保护下,20.0mmol上步制备的Int-4溶于50mL干燥的THF,降温至-78℃,滴加入24.0mmol的2.5M正丁基锂正己烷溶液,搅拌反应10分钟,再滴加入25.0mmol的硼酸三甲酯,搅拌反应30分钟,升至室温搅拌反应1小时,滴加入20mL的3M稀盐酸,分出有机相,水相用乙酸乙酯萃取,有机相合并用饱和盐水洗,干燥,过滤,滤液减压浓缩干,向残余物内加入20mL的正己烷,过滤,滤饼用正己烷洗,得到化合物Int-5,黄色固体,收率84%。
第六步:化合物J569的制备
在氮气保护下,22.0mmol上步制备的Int-5、20.0mmol的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪和60mL的甲苯混合,再加入60.0mmol的无水碳酸钾、0.02mmol的Pd(PPh3)4催化剂、30mL的水和30mL的乙醇,升温回流搅拌反应15小时,降至室温,加入50mL水,分出有机相,水相用二氯甲烷萃取,合并有机相,干燥,过滤,滤液减压浓缩干燥,用硅胶柱分离纯化,再用二氯甲烷/乙醇重结晶,得到化合物J569(X=O),白色固体,收率85%,MS(TOF)m/z:653.2281[M+H];1HNMR(δ、CDCl3):8.48(1H,s);8.38~8.34(4H,m);8.14~8.12(2H,m);7.96~7.94(2H,m);7.91~7.89(1H,d);7.85~7.82(2H,m);7.80~7.74(2H,m);7.71~7.67(1H,m);7.56~7.47(8H,m);7.45~7.38(3H,m);7.26~7.24(2H,m)。
参照上述类似的合成方法制备X=S的化合物,仅将第一步的sub-2替换为2-(2,2-二氟-1-((三甲基硅基)氧)乙烯基)苯硫酚,白色固体,收率81%,MS(TOF)m/z:669.2047[M+H];1HNMR(δ、CDCl3):8.48(1H,s);8.38~8.34(4H,m);8.14~8.09(4H,m);8.01~7.99(1H,d);7.97~7.95(2H,m);7.83~7.81(1H,d);7.75~7.69(2H,m);7.56~7.47(8H,m);7.45~7.38(3H,m);7.26~7.24(2H,m)。
实施例2~实施例93
参照上述类似的合成方法,制备以下表1所示化合物:
表1
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实施例94
化合物J653的制备方法,以X=O为例,包括如下步骤:
第一步:中间体Int-6的制备
在氮气保护下,20.0mmol的sub-3、24.0mmol的sub-4溶于50mL的1,2-二氯乙烷,再加入40.0mmol的三氟甲烷磺酸,升温至90℃,搅拌反应10小时,冷却到室温,减压浓缩干燥,用硅胶柱分离纯化,得到化合物Int-6,黄色固体,收率:68%。
第二步:中间体Int-7的制备
参照实施例1第二步的合成方法,仅将实施例1第二步的Int-1替换为Int-6,制备化合物Int-7,黄色固体,收率89%。
第三步:中间体Int-8的制备
20.0mmol上步制备的Int-7溶于100mL的二甲苯中,加入0.1mol的二氧化锰,升温至回流搅拌反应15小时,降至室温,过滤,滤饼用二氯甲烷洗,滤液减压浓缩干燥,硅胶柱分离纯化,得到化合物Int-8,黄色固体,收率95%。
第四步:中间体Int-9的制备
在氮气保护下,20.0mmol上步制备的Int-8溶于60mL的DMF,加入24.0mmol的联硼酸频哪醇酯、30.0mmol的无水醋酸钾、2.0mmol的碘化亚铜和0.2mmol的催化剂PdCl2(dppf)CH2Cl2,升温至100℃,搅拌反应15小时,降至室温,加入150mL冰水,过滤,滤饼用水洗,固体用硅胶柱分离纯化,得到化合物Int-9,黄色固体,收率86%。
第五步:化合物J653的制备
在氮气保护下,22.0mmol上步制备的Int-9、20.0mmol的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪和60mL的甲苯混合,再加入60.0mmol的无水碳酸钾、0.02mmol的Pd(PPh3)4催化剂、30mL的水和30mL的乙醇,升温回流搅拌反应15小时,降至室温,加入50mL水,分出有机相,水相用二氯甲烷萃取,合并有机相,干燥,过滤,滤液减压浓缩干燥,用硅胶柱分离纯化,再用二氯甲烷/乙醇重结晶,得到化合物J653(X=O),黄色固体,收率86%,MS(TOF)m/z:654.2234[M+H];1HNMR(δ、CDCl3):9.08(1H,s);8.48~8.45(1H,m);8.38~8.34(4H,m);8.14~8.12(1H,d);8.03~8.01(1H,d);7.98~7.96(2H,m);7.83~7.80(2H,m);7.75(1H,s);7.57~7.49(7H,m);7.45~7.38(5H,m);7.26~7.24(2H,m)。
参照上述类似的合成方法制备X=S的化合物,仅将第一步的sub-4替换为5-氯-2-(2,2-二氟-1-((三甲基硅基)氧)乙烯基)苯硫酚,黄色固体,收率84%,MS(TOF)m/z:670.2001[M+H];1HNMR(δ、CDCl3):9.08(1H,s);8.48~8.45(1H,m);8.38~8.34(4H,m);8.25~8.20(2H,m);8.18~8.12(2H,m);7.98~7.96(2H,m);7.82~7.81(1H,d);7.58~7.50(7H,m);7.45~7.38(5H,m);7.26~7.24(2H,m)。
实施例95~实施例117
参照上述类似的合成方法,制备以下表2所示化合物:
表2
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上述实施例中,X为O或S;T选自O、S、CMe2、CPh2、NPh、NPhPh;
Me为甲基,Ph为苯基,PhPh为联苯基。
实施例118
一种OLED元件,如图1所示,本实施例的OLED元件为顶发射光元件,包括基板101、设于基板101上的阳极102、设于阳极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上的有机发光层106、设于有机发光层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以及设于电子注入层109上的阴极110和阴极之上的封盖层111,不包含空穴阻挡层107的OLED元件的制备方法包括如下步骤:
1)将涂布了ITO导电层的玻璃基板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,抽真空至小于1×10-5Pa,在上述ITO膜上蒸镀金属银作为阳极,蒸镀膜厚为继续分别蒸镀化合物HI01和F4TCNQ作为空穴注入层,其中,F4TCNQ为HI01质量的3%,蒸镀膜厚为/>
3)在上述空穴注入层上继续蒸镀化合物HTM为空穴传输层,蒸镀膜厚为
4)在上述空穴传输层上继续蒸镀化合物EBL为电子阻挡层,蒸镀膜厚为
5)在电子阻挡层上继续蒸镀化合物RH020作为主体材料和RD011为掺杂材料,RD011为化合物RH020质量的3%,作为元件的有机发光层,蒸镀所得有机发光层的膜厚为
6)在有机发光层上继续蒸镀一层LiQ和本发明的式(I)化合物作为元件的电子传输层,其中,本发明的式(I)化合物为LiQ质量的50%,蒸镀膜厚为
7)在电子传输层之上继续蒸镀一层LiF为电子注入层,蒸镀膜厚为
8)在电子注入层之上蒸镀金属镁和银作为元件的透明阴极层,镁和银的质量比为1:10,蒸镀膜厚为
9)在透明阴极层之上再蒸镀一层CPD作为元件的CPL层,蒸镀膜厚为得到本发明提供的OLED元件。
上述实施例118中使用的化合物结构如下:
实施例119
一种有机电致发光元件200,其结构如图2所示,其包含衬底201、阳极202、空穴注入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。
对比例1
按照与实施例118相同的步骤,将步骤6)中本发明的式(I)化合物替换为E01,得到对比元件1;
对上述过程制备的有机电致发光元件进行如下性能测试:
使用数字源表及亮度计测定实施例118、119及对比例1中制备得到的有机电致发光元件的驱动电压和电流效率以及元件的寿命。具体而言,以每秒0.1V的速率提升电压,测定当有机电致发光元件的亮度达到1000cd/m2时的电压即驱动电压,同时测出此时的电流密度;亮度与电流密度的比值即为电流效率;LT95%寿命测试如下:使用亮度计在1000cd/m2亮度下,保持恒定的电流,测量有机电致发光元件的亮度衰减为950cd/m2的时间,单位为小时。表3中列出的数据是相较于对比元件1的相对数据。
表3
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由表3可知,本发明的杂环化合物制备的元件在相同的亮度下,驱动电压相较E01更低,电流效率提高明显,最高达到对比元件的1.23倍之多,而且元件的LT95%寿命有较好的改善,表明本发明的杂环化合物是性能优异的电子传输层材料。
对比例1中的化合物E01与本发明的化合物相比,区别在于E01在轴向的空间位阻较大,导致驱动电压偏高、效率低。而本发明的杂环化合物在极化轴方向的位阻小,共轭能力强,其在分子成膜及电荷的传输上性能更优异,因此元件内电荷的传输更加平衡,元件性能得到显著提高。
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)
1.一种杂环化合物,其特征在于,其结构式如式(I)所示:
其中,
L1、L2各自独立地选自由单键、取代或未取代的C6-C60亚芳基、或者取代或未取代的C2-C60亚杂芳基组成的群组;
X1、X2、X3、X4、X5、X6各自独立地表示CR1或N;
G表示O、S、SO、SO2、Se、CR2R3、SiR2R3或NAr3;
R1、R2、R3各自独立地选自由氢、氘、氟、腈基、取代或未取代的C1-C40烷基、取代或未取代的C1-C40烷氧基、取代或未取代的C2-C40烯基、取代或未取代的C1-C40烷硫基、取代或未取代的C1-C40烷氧基、取代或未取代的C3-C40环烷基、取代或未取代的C1-C40烷基亚砜基、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芳硫基、取代或未取代的C6-C60芳基亚砜基、取代或未取代的C3-C40甲硅烷基、取代或未取代的硼基、取代或未取代的胺基、取代或未取代的芳基膦基、取代或未取代的氧化膦基、或者取代或未取代的C2-C60杂环芳基组成的群组;任意相邻的两个或多个取代基可以任意的接合或稠合形成取代或未取代的环;
Ar1、Ar2、Ar3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。
2.根据权利要求1所述的杂环化合物,其特征在于,所述杂环化合物选自由以下结构组成的群组:
其中,X1~X6、Ar1、Ar2、L1、L2和G的含义与权利要求1的定义相同。
3.根据权利要求1所述的杂环化合物,其特征在于,所述R1、R2、R3各自独立地选自由氢、氘、甲基、取代或未取代的苯基、取代或未取代的芴基组成的群组;
Ar1、Ar2、Ar3各自独立地选自由取代或未取代的以下基团组成的群组: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、吲哚并咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、苯并咔唑基、二苯并咔唑基、氮杂二苯并[g,ij]萘并[2,1,8-cde]薁、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。
4.根据权利要求1所述的杂环化合物,其特征在于,所述G选自O或S;
X1为N和/或X1~X6为CR1;
R1选自氢、氘、氟或腈基。
5.根据权利要求1所述的杂环化合物,其特征在于,所述L1、L2各自独立地选自单键或由以下III-1~III-23所示基团组成的群组:
其中,虚线代表基团的连接位点。
6.根据权利要求1-5中任一项所述的杂环化合物,其特征在于,所述杂环化合物选自如下式J544-J660所示的化合物:
其中,T选自O、S、SO、Se、CMe2、CPh2、NPh、NPhPh;
X选自O或S;
Me表示甲基、Ph表示苯基、PhPh表示联苯基。
7.权利要求1-6中任一项所述的杂环化合物在制备有机电致发光元件中的应用。
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;所述有机层或封盖层中的至少一层的材料包括权利要求1-6中任一项所述的杂环化合物。
9.根据权利要求8所述的有机电致发光元件,其特征在于,所述有机层包括空穴注入层、空穴传输层、空穴阻挡层、发光层、电子传输层、电子注入层或电子阻挡层;所述发光层、电子传输层或空穴阻挡层包括权利要求1-6中任一项所述的杂环化合物。
10.一种消费型产品,其特征在于,其包括权利要求8所述的有机电致发光元件。
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