CN105102460B - 有机电气元件用化合物、利用其的有机电气元件及其电子装置 - Google Patents
有机电气元件用化合物、利用其的有机电气元件及其电子装置 Download PDFInfo
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Abstract
本发明提供可提高元件的发光效率、稳定性及寿命的最新化合物及利用该化合物的有机电气元件及其电子装置。
Description
技术领域
本发明涉及有机电气元件用化合物、利用其的有机电气元件及其电子装置。
背景技术
通常,有机发光现象是指,利用有机物质将电能转换为光能的现象。利用有机发光现象的有机电气元件通常具有阳极、阴极及它们之间包括有机物层的结构。在此,有机物层为了提高有机电气元件的效率和稳定性而普遍形成为由各种不同物质构成的多层结构,例如,可以由空穴注入层、空穴输送层、发光层、电子输送层及电子注入层等形成。
在有机电气元件中,用作有机物层的材料可根据功能来分为发光材料和电荷输送材料,例如,空穴注入材料、空穴输送材料、电子输送材料及电子注入材料等。
另一方面,应解决导致有机电气元件寿命缩短的问题之一的金属氧化物从阳极电极(ITO)向有机层渗透扩散的现象,应实现对于元件驱动时所产生的焦耳热(Jouleheating)的稳定的特性,即,需要开发具有高玻璃化转变温度的空穴注入层材料。空穴输送层材料的低玻璃化转变温度具有在元件驱动时降低薄膜表面的均匀度的特性,据悉,这种特性会对元件寿命产生大影响。并且,有机发光二极管(OLED)主要借助沉积方法而形成,目前需要开发一种在沉积时可长时间承受的材料,即,具有强耐热特性的材料。
为了充分发挥上述有机电气元件所具有的优秀特征,应先行保障形成元件内有机物层的物质如空穴注入物质、空穴传输物质、发光物质、电子传输物质、电子注入物质等以稳定、有效的材料作为基础,但当前处于未充分开发稳定、有效的有机电气元件用有机物层材料的状态,因而开发新的材料持续成为一种需求。
发明内容
本发明的目的在于提供一种具有高发光效率、低驱动电压、高耐热性,并且可提高色纯度及寿命的化合物,以及利用该化合物的有机电气元件及其电子装置。
在一实施方式中,本发明提供由以下化学式表示的化合物:
在另一实施方式中,本发明提供利用由上述化学式表示的化合物的有机电气元件及其电子装置。
利用本发明的化合物,可以实现元件的高发光效率、低驱动电压、高耐热性,可大幅提高元件的色纯度及寿命。
附图说明
图1为本发明的有机电致发光元件的例示图。
具体实施方式
以下,参照附图对本发明的实施例进行详细说明。
在对各附图的结构要素附加附图标记的过程中,要留意相同的结构要素即使显示于不同的附图上,也尽可能地赋予相同的附图标记。并且,在对本发明进行说明的过程中,在判断相关的公知结构或功能的具体说明会模糊本发明的要旨的情况下,将省略详细说明。
在说明本发明的结构要素的过程中,可使用第一、第二、A、B、(a)、(b)等术语。这种术语仅用于与其他结构要素相互区别,相关结构要素的本质、次序或顺序等不会因这种术语而受到限制。在一个结构要素与另一结构要素“连接”、“结合”或“联接”的情况下,其结构要素既可以与另一结构要素直接连接或联接,但也可以理解为在各结构要素之间“连接”、“结合”或“联接”有其他结构要素。
在本说明书中所使用的术语“卤代”或“卤素”只要没有不同的说明,就是氟(F)、溴(Br)、氯(Cl)或碘(I)。
只要没有其他说明,在本发明中所使用的术语“烷”或“烷基”的碳的数量为1至60,但并不限定于此。
只要没有其他说明,在本发明中所使用的术语“烯基”或“炔基”分别具有碳的数量为2至60的双键或三键,但并不限定于此。
在本发明中所使用的术语“环烷基”只要没有其他说明,就意味着形成具有3至60的碳数的环的烷,但并不局限于此。
在本发明中所使用的术语“烷氧基”意味着附着有氧自由基的烷基,只要没有其他说明,就具有1至60的碳数,但并不局限于此。
在本发明中所使用的术语“芳基”及“亚芳香基”只要没有别的说明,就分别具有6至60的碳数,但并不局限于此。
在本发明中,芳基或亚芳香基意味着单环或多重环的芳香族,并包括相邻的取代基相结合或参与反应来形成的芳香族环。例如,芳基可以为苯基、联苯基、芴基、螺芴基及螺二芴基。
在本发明中所使用的术语“杂烷基”,除非另行说明,否则表示包含至少一个杂原子的烷基。在本发明中所使用的术语“杂芳基”或“杂亚芳基”只要没有别的说明,就意味着分别包含至少一种的杂原子的碳数2至60的芳基或亚芳香基,但并不局限于此,可以包含单环及多环中的至少一种,并由相邻的官能团结合而成。
只要没有其他说明,在本发明中所使用的术语“杂环烷基”、“杂环基”包含一个或一个以上的杂原子,碳的数量为2至60,不仅包含单环,而且还包含多重环,并且还可通过相邻的基相结合来形成。并且,“杂环基”可意味着包含杂原子的脂环族和/或芳香族。
在本说明书中所使用的术语“杂原子”只要没有别的说明,就表示N、O、S、P或Si。
只要没有其他说明,在本发明中所使用的术语“脂肪族”意味着碳数1至60的脂肪烃,“脂肪族环”意味着碳数3至60的脂肪族碳氢化合物环。
只要没有其他说明,在本发明中所使用的术语“饱和或不饱和环”意味着饱和脂肪族环或不饱和脂肪族环,或者碳的数量为6至60的芳香族环或者杂环。
除了上述的杂环化合物之外,除此之外的其他杂环化合物或杂环基还包含至少一种杂原子,但并不局限于此。
并且,只要没有明确的说明,在本发明中所使用的术语“取代或非取代”中,“取代意味着被选自由重氢、卤素、氨基、腈基、硝基、C1-C20的烷基、C1-C20的烷氧基、C1-C20的烷基胺、C1-C20的烷基噻吩、C6-C20的芳噻吩、C2-C20的烯基、C2-C20的炔基、C3-C20的环烷基、C6-C60的芳基、芴基、被重氢所取代的C6-C20的芳基、C8-C20的芳烯基、硅烷基、硼基、锗基及包含选自由O、N、S、Si及P组成的组的至少一种杂原子的C2-C20的杂环基组成的组的至少一种取代基所取代,但并不局限于这些取代基。
图1为本发明的一实施例的有机电气元件的例示图。
参照图1,本发明的一实施例的有机电气元件100包括:第一电极120、第二电极180,形成于基板110上;以及有机物层,在第一电极120和第二电极180之间包含本发明的化合物。此时,第一电极120可以为Anode(阳极),第二电极180可以为Cathode(阴极),在倒置型的情况下,第一电极可以为阴极,第二电极可以为阳极。
有机物层可在第一电极120上依次包括空穴注入层130、空穴输送层140、发光层150、电子输送层160及电子注入层170。此时,除了发光层150之外,剩余的层可以无需形成。还可以包括空穴阻挡层、电子阻挡层、发光辅助层151、缓冲层141等,也可以由电子输送层160等执行空穴阻挡层的作用。
并且,虽未图示,但本发明的一实施例的有机电气元件还可以包括形成于第一电极和第二电极中的至少一面中与上述有机物层相反的一面的保护层。
适用于上述有机物层的本发明的化合物可用作空穴注入层130、空穴传输层140、电子传输层160、电子注入层170、发光层150的主体或掺杂物,或者可用作包覆层的材料。
本发明的一实施例的有机电致发光元件,可利用物理气相沉积(physical vapordeposition)方法来制备。例如,在基板上沉积金属或具有导电性的金属氧化物或它们的合金来形成阳极120,在上述阳极120的上部形成包含空穴注入层130、空穴输送层140、发光层150、电子输送层160及电子注入层170的有机物层后,在上述有机物层的上部沉积可用作阴极180的物质来完成制备。
并且,有机物层使用多种高分子材料,通过并非蒸镀法的溶液工序或溶剂精制法(solvent process),例如,旋涂工序、喷嘴印刷工序、喷墨打印工序、狭缝涂布工序、浸涂工序、卷对卷工序、刮涂工序、丝网印刷工序或热转印方法等方法来制成为更少数量的层。由于本发明的有机物层能够由多种方法形成,因此,本发明的保护范围不会因形成方法而受到限制。
本发明的一实施例的有机电气元件可根据所使用的材料分为前面发光型、后面发光型或双面发光型。
并且,本发明的一实施例的有机电气元件可以为有机电致发光元件、有机太阳能电池、有机感光体、有机晶体管、单色或白色照明用元件中的一种。
本发明的另一实施例可包括电子装置,上述电子装置包括:显示装置,包括上述本发明的有机电气元件;以及控制部,用于控制上述显示装置。此时,电子装置可以为当前或未来的有无线通信终端,并包括手机等移动通信终端、PDA、电子词典、PMP、遥控器、导航仪、游戏机、各种TV、各种计算机等所有电子装置。
以下,对本发明的一实施方式的化合物进行说明。
本发明的一实施方式的化合物由以下化学式1表示。
<化学式1>
在上述化学式中,
m、n及o分别为1~4的整数。
R1至R3可相互独立地选自由氢、重氢、超重氢、C6-C60的芳基、包含O、N、S、Si及P中的至少一种杂原子的C2-C60的杂环基、C1-C50的烷基、芴基及-L1-N(Ar2)(Ar3)组成的组。
并且,R1至R3可分别通过相邻的基之间相互结合来形成至少一种环。此时,不形成环的R1至R3可分别以与上述的定义相同的方式进行定义。例如,在m和n均为2的情况下,可通过相邻的R1之间相互结合来形成环,R2即使相邻,也可相互独立地成为芳基或杂环基。
当然,在m为大于2的整数的情况下,多个R1可相同或相异,在相邻的基中,一部分基相互结合来形成环,而剩余的不形成环的基可从在上述中定义的取代基组中进行选择。在n或o为大于2的整数的情况下,也与上述相同。
另一方面,通过相邻的基之间相互结合来形成的环可以为C3-C60的脂肪族环、C6-C60的芳香族环、C2-C60的杂环或由它们的组合形成的稠环等,不仅可以为单环或多重环,还可以为饱和环或不饱和环。
X可以为NR4或O(氧),在这里,R4可选自由C6-C60的芳基、包含O、N、S、Si及P中的至少一种杂原子的C2-C60的杂环基、C1-C50的烷基、芴基、及-L1-N(Ar2)(Ar3)组成的组。
Ar1选自由C6-C60的芳基、包含O、N、S、Si及P中的至少一种杂原子的C2-C60的杂环基、C1-C50的烷基、芴基、及-L1-N(Ar2)(Ar3)组成的组。
此时,Ar2及Ar3可相互独立地选自由C6-C60的芳基、包含O、N、S、Si及P中的至少一种杂原子的C2-C60的杂环基、C1-C50的烷基及芴基组成的组。
上述L1可选自由单键、C6-C60的亚芳香基、包含O、N、S、Si及P中的至少一种杂原子的C2-C60的杂芳基、以及芴乙烯基组成的组,它们(除单键)可分别被选自由硝基、氰基、卤代基、C1-C20的烷基、C6-C20的芳基、C2-C20的杂环基、C1-C20的烷氧基及氨基组成的组中的一种以上的取代基来取代。
并且,上述化学式1可由下述化学式中的一个来表示。
此时,上述化学式2至化学式4中的R1至R4、X、m、n及o可与上述化学式1中的定义相同。
Ar4能够选自由C6-C60的芳基、包含O、N、S、Si及P中的至少一种杂原子的C2-C60的杂环基、C1-C50的烷基及芴基组成的组。
并且,Z1至Z4分别独立地表示CR5或N,其中,R5能够选自由氢、C6-C60的芳基、包含O、N、S、Si及P中的至少一种杂原子的C2-C60的杂环基、C1-C50的烷基、及芴基组成的组。
上述芳基、芴基、杂环基及烷基可分别被选自由重氢、卤素、硅烷基、硼基、锗基、氰基、硝基、C1-C20的烷硫基、C1-C20的烷氧基、C1-C20的烷基、C2-C20的烯基(alkenyl)、C2-C20的炔基(alkynyl)、C6-C20的芳基、被重氢取代的C6-C20的芳基、C2-C20的杂环基、C3-C20的环烷基、C7-C20的芳基烷基及C8-C20的芳烯基组成的组中的一种以上取代基来取代。
在这里,在上述芳基的情况下碳的数量为6~60,优选地,芳基可以为碳的数量为6~30的芳基,更优选地,芳基可以为碳的数量为6~20的芳基,
在上述杂环基的情况下碳的数量为2~60,优选地,杂环基可以为碳的数量为2~30的杂环,更优选地,杂环基可以为碳的数量为2~20的杂环,
在上述亚芳香基的情况下碳的数量为6~60,优选地,亚芳香基可以为碳的数量为6~30的亚芳香基,更优选地,亚芳香基可以为谈的数量为6~20的亚芳香基,
在上述烷基的情况下碳的数量为1~50,优选地,烷基可以为碳的数量为1~30的烷基,更优选地,烷基可以为碳的数量为1~20的烷基,尤为优选地,烷基可以为碳的数量为1~10的烷基。
另一方面,上述化学式1可以为下述化合物中的一个。
以下,举出实施例来对本发明的由化学式1表示的化合物的合成例及有机电气元件的制备例进行具体说明,但本发明并不局限于以下的实施例。
合成例
本发明的以化学式1表示的化合物(Product)如以下化学式1,通过使Sub 1与Sub2反应来制备,但不受此限定。
<反应式1>
1.Sub 1的合成例
上述反应式1中的Sub 1可由下述反应式2和反应式3的反应途径来合成。
<反应式2>
中间体Sub 1-2的合成
向Sub 1-1(1当量)放入2,2,6,6-tetramethylpiperidine(1.2当量),并在THF中进行溶解后,将反应物的温度降低至-78℃。向反应物慢慢滴加n-BuLi(2.5M in hexane)(1.1当量)并搅拌30分钟。之后,重新将反应物的温度降低至-78℃,并滴加Triisopropylborate(1.5当量)。在常温状态下对反应物进行搅拌后,放入水来进行稀释,并放入2N的HCl。若反应结束,则在使用ethyl acetate和水进行提取之后,使用MgSO4进行干燥、浓缩,并对所生成的有机物进行silicagel column及再结晶,从而得到Sub 1-2。
中间体Sub 1-3的合成
在将Sub 1-2(1当量)、溴化合物(1当量)、Pd(PPh3)4(0.03当量)、NaOH(3当量)溶解于无水THF和少量的水之后,使反应物形成24小时的环流。若反应结束,则将反应物的温度降低至常温,使用CH2Cl2进行提取,并用水清洗。在使用无水MgSO4去除少量的水,并进行减压过滤后,采用柱层析法对通过浓缩有机溶剂来生成的生成物进行分离,从而得到了所需的Sub 1-3。
中间体Sub 1-4的合成
将Sub 1-3和triphenylphosphine溶解于o-dichlorobenzene,并使反应物形成24小时的环流。若反应结束,则在通过减压蒸馏来去除溶剂后,采用柱层析法对被浓缩的生成物进行分离,从而得到了所需的Sub 1-4。
中间体Sub 1-6的合成
添加Sub 1-4(1当量)、Sub 1-5(1.1当量)、Pd2(dba)3(0.3当量)、50%P(t-Bu)3(9当量)、NaOt-Bu(3当量),并在40℃的温度下进行搅拌。若反应结束,则在使用CH2Cl2和水进行提取后,对在使用MgSO4进行干燥、浓缩后所生成的化合物进行silicagel column及再结晶,从而得到Sub1-6。
中间体Sub 1-7的合成
在将Sub 1-6(1当量)、溴化合物(1当量)、Pd(PPh3)4(0.03当量)、NaOH(3当量)溶解于无水THF和少量的水之后,使反应物形成24小时的环流。若反应结束,则将反应物的温度降低至常温,使用CH2Cl2进行提取,并用水清洗。在使用无水MgSO4去除少量的水,并进行减压过滤后,采用柱层析法对通过浓缩有机溶剂来生成的生成物进行分离,从而得到了所需的Sub 1-7。
Sub 1(A)的合成
将Sub 1-7和triphenylphosphine溶解于o-dichlorobenzene,并使反应物形成24小时的环流。若反应结束,则在通过减压蒸馏来去除溶剂后,采用柱层析法对被浓缩的生成物进行分离,从而得到了所需的Sub 1(A)。
<反应式3>
中间体Sub 1-9的合成
在圆底烧瓶中,使用DMF溶解Sub 1-8(1当量)后,添加Bis(pinacolato)diboron)(1.1当量)、Pd(dppf)Cl2(0.03当量)、KOAc(3当量),并在90℃的温度下进行搅拌。若反应结束,则通过蒸馏来去除DMF,并使用CH2Cl2和水进行提取。对在使用MgSO4进行干燥、浓缩后所生成的化合物进行silicagel column及再结晶,从而得到Sub 1-9。
中间体Sub 1-10的合成
将Sub 1-9(1当量)、溴化合物(1当量)、Pd(PPh3)4(0.03当量)、K2CO3(3当量)溶解于无水THF和少量的水之后,使反应物形成24小时的环流。若反应结束,则将反应物的温度降低至常温,使用CH2Cl2进行提取,并用水清洗。在使用无水MgSO4去除少量的水,并进行减压过滤后,采用柱层析法对通过浓缩有机溶剂来生成的生成物进行分离,从而得到了所需的Sub 1-10。
Sub 1(B)的合成
将Sub 1-10和triphenylphosphine溶解于o-dichlorobenzene,并使反应物形成24小时的环流。若反应结束,则在通过减压蒸馏来去除溶剂后,采用柱层析法对被浓缩的生成物进行分离,从而得到了所需的Sub 1(B)。
另一方面,Sub 1的例示如下,但不受此限定,其FD-MS如下表1所示。
【表1】
化合物 | FD-MS | 化合物 | FD-MS |
Sub 1(1) | m/z=382.15(C28H18N2=382.46) | Sub 1(2) | m/z=432.16(C32H20N2=432.51 |
Sub 1(3) | m/z=432.16(C32H20N2=432.51) | Sub 1(4) | m/z=458.18(C34H22N2=458.55) |
Sub 1(5) | m/z=537.20(C37H23N5=537.61) | Sub 1(6) | m/z=537.20(C37H23N5=537.61) |
Sub 1(7) | m/z=536.20(C38H24N4=536.62) | Sub 1(8) | m/z=536.20(C38H24N4=536.62) |
Sub 1(9) | m/z=536.20(C38H24N4=536.62) | Sub 1(10) | m/z=613.23(C43H27N5=613.71) |
Sub 1(11) | m/z=612.23(C44H28N4=612.72) | Sub 1(12) | m/z=612.23(C44H28N4=612.72) |
Sub 1(13) | m/z=574.22(C41H26N4=574.67) | Sub 1(14) | m/z=498.18(C35H22N4=498.58) |
Sub 1(15) | m/z=549.22(C40H27N3=549.66) | Sub 1(16) | m/z=383.13(C28H17NO=383.44) |
Sub 1(17) | m/z=383.13(C28H17NO=383.44) | Sub 1(18) | m/z=474.17(C34H22N2O=474.55) |
Sub 1(19) | m/z=550.20(C40H26N2O=550.65) | Sub 1(20) | m/z=307.10(C22H13NO=307.34) |
2.Sub 2的例
Sub 2的例示如下,但不受此限定,它们的FD-MS如下表2所示。
【表2】
化合物 | FD-MS | 化合物 | FD-MS |
Sub 2-1 | m/z=155.96(C6H5Br=157.01) | Sub 2-2 | m/z=205.97(C10H7Br=207.07) |
Sub 2-3 | m/z=205.97(C10H7Br=207.07) | Sub 2-4 | m/z=231.99(C12H9Br=233.10) |
Sub 2-5 | m/z=231.99(C12H9Br=233.10) | Sub 2-6 | m/z=308.02(C18H13Br=233.10) |
Sub 2-7 | m/z=255.99(C14H9Br=257.13) | Sub 2-8 | m/z=255.99(C14H9Br=257.13) |
Sub 2-9 | m/z=311.01(C15H10BrN3=312.16) | Sub 2-10 | m/z=311.01(C15H10BrN3=312.16) |
Sub 2-11 | m/z=310.01(C16H11BrN2=311.18) | Sub 2-12 | m/z=310.01(C16H11BrN2=311.18) |
Sub 2-13 | m/z=232.98(C11H8BrN=234.09) | Sub 2-14 | m/z=310.01(C16H11BrN2=311.18) |
Sub 2-15 | m/z=387.04(C21H14BrN3=388.26) | Sub 2-16 | m/z=386.04(C22H15BrN2=387.27) |
Sub 2-17 | m/z=386.04(C22H15BrN2=387.27) | Sub 2-18 | m/z=348.03(C19H13BrN2=349.22) |
Sub 2-19 | m/z=271.99(C13H9BrN2=273.13) | Sub 2-20 | m/z=283.00(C15H10BrN=284.15) |
Sub 2-21 | m/z=475.09(C30H22BrN=476.41) | Sub 2-22 | m/z=515.12(C33H26BrN=516.47) |
Sub 2-23 | m/z=639.16(C43H30BrN=640.61) | Sub 2-24 | m/z=637.14(C43H28BrN=638.59) |
Sub 2-25 | m/z=505.05(C30H20BrNS=506.46) | Sub 2-26 | m/z=240.05(C14H9ClN2=240.69) |
Sub 2-27 | m/z=258.04(C14H8ClFN2=258.68) | Sub 2-28 | m/z=290.06(C18H11ClN2=290.75) |
Sub 2-29 | m/z=290.06(C18H11ClN2=290.75) | Sub 2-30 | m/z=366.09(C24H15ClN2=366.84) |
Sub 2-31 | m/z=366.09(C24H15ClN2=366.84) | Sub 2-32 | m/z=366.09(C24H15ClN2=366.84) |
Sub 2-33 | m/z=241.04(C13H8ClN3=241.68) | Sub 2-34 | m/z=316.08(C20H13ClN2=316.78) |
Sub 2-35 | m/z=316.08(C20H13ClN2=316.78) | Sub 2-36 | m/z=392.11(C26H17ClN2=392.88) |
Sub 2-37 | m/z=392.11(C26H17ClN2=392.88) | Sub 2-38 | m/z=356.11(C23H17ClN2=356.85) |
Sub 2-39 | m/z=329.07(C20H12ClN3=329.78) | Sub 2-40 | m/z=405.10(C26H16ClN3=405.88) |
Sub 2-41 | m/z=346.03(C20H11ClN2S=346.83) | Sub 2-42 | m/z=330.06(C20H11ClN2O=330.77) |
Sub 2-43 | m/z=372.08(C22H17ClN2Si=372.92) | Sub 2-44 | m/z=422.06(C26H15ClN2S=422.93) |
Sub 2-45 | m/z=406.09(C26H15ClN2O=406.86) | Sub 2-46 | m/z=448.12(C28H21ClN2Si=449.02 |
Sub 2-47 | m/z=268.08(C16H13ClN2=268.74) | Sub 2-48 | m/z=420.14(C28H21ClN2=344.84) |
Sub 2-49 | m/z=420.14(C28H21ClN2=420.93) | Sub 2-50 | m/z=317.07(C19H12ClN3=317.77) |
Sub 2-51 | m/z=318.07(C18H11ClN4=318.76) | Sub 2-52 | m/z=317.07(C19H12ClN3=317.77) |
Sub 2-53 | m/z=316.08(C20H13ClN2=316.78) | Sub 2-54 | m/z=366.09(C24H15ClN2=366.84) |
Sub 2-55 | m/z=245.08(C14H4D5ClN2=245.72) | Sub 2-56 | m/z=320.10(C20H5D4ClN2=320.81) |
Sub 2-57 | m/z=320.10(C20H5D4ClN2=320.81) | Sub 2-58 | m/z=320.10(C20H5D4ClN2=320.81) |
Sub 2-59 | m/z=397.14(C26H12D5ClN2=397.9) | Sub 2-60 | m/z=410.15(C27H15D4ClN2=410.93) |
Sub 2-61 | m/z=396.13(C26H13D4ClN2=396.9) | Sub 2-62 | m/z=240.05(C14H9ClN2=240.69) |
Sub 2-63 | m/z=290.06(C18H11ClN2=290.75) | Sub 2-64 | m/z=316.08(C20H13ClN2=316.78) |
Sub 2-65 | m/z=432.14(C29H21ClN2=432.94) |
3.Products的合成例
在向圆底烧瓶放入Sub 1(1当量)、Sub 2(1.2当量)、Pd2(dba)3(0.05当量)、P(t-Bu)3(0.1当量)、NaOt-Bu(3当量)、toluene(10.5mL/1mmol)后,在100℃的温度下使反应物发生反应。若反应结束,则在使用ether和水进行提取后,对在使用MgSO4进行干燥、浓缩后所生成的有机物进行silicagel column及再结晶,从而得到生成物Product。
(1)1-1的合成例
在向圆底烧瓶放入5-phenyl-5,10-dihydrobenzo[a]indolo[2,3-c]carbazole(7.6g,20mmol)、bromobenzene(3.7g,24mmol)、Pd2(dba)3(0.03~0.05mmol)、P(t-Bu)3(0.1当量)、NaOt-Bu(3当量)、toluene(10.5mL/1mmol),在100℃的温度下使反应物发生反应。若反应结束,则在使用ether和水进行提取后,对在使用MgSO4进行干燥、浓缩后所生成的有机物进行silicagel column及再结晶,从而得到6.2g的生成物(收率68%)。
(2)1-29的合成例
在向圆底烧瓶放入10H-benzo[a]benzofuro[2,3-c]carbazole(6.1g,20mmol)、5-bromo-2,4-diphenylpyrimidine(7.5g,24mmol)、Pd2(dba)3(0.03~0.05mmol)、P(t-Bu)3(0.1当量)、NaOt-Bu(3当量)、toluene(10.5mL/1mmol),在100℃的温度下使反应物发生反应。若反应结束,则在使用ether和水进行提取后,对在使用MgSO4进行干燥、浓缩后所生成的有机物进行silicagel column及再结晶,从而得到6.6g的生成物(收率61%)。
(3)2-1的合成例
在向圆底烧瓶放入5-phenyl-5,10-dihydrobenzo[a]indolo[2,3-c]carbazole(7.6g,20mmol)、2-chloro-4-phenylquinazoline(5.8g,24mmol)、Pd2(dba)3(0.03~0.05mmol)、P(t-Bu)3(0.1当量)、NaOt-Bu(3当量)、toluene(10.5mL/1mmol),在100℃的温度下使反应物发生反应。若反应结束,则在使用ether和水进行提取后,对在使用MgSO4进行干燥、浓缩后所生成的有机物进行silicagel column及再结晶,从而得到7.9g的生成物(收率67%)。
(4)2-46的合成例
在向圆底烧瓶放入10H-benzo[a]benzofuro[2,3-c]carbazole(6.1g,20mmol)、2-chloro-4-phenylpyrido[3,2-d]pyrimidine(5.8g,24mmol)、Pd2(dba)3(0.03~0.05mmol)、P(t-Bu)3(0.1当量)、NaOt-Bu(3当量)、toluene(10.5mL/1mmol),在100℃的温度下使反应物发生反应。若反应结束,则在使用ether和水进行提取后,对在使用MgSO4来对有机层进行干燥、浓缩后所生成的有机物进行silicagel column及再结晶,从而得到5.9g的生成物(收率58%)。
【表3】
化合物 | FD-MS | 化合物 | FD-MS |
1-1 | m/z=458.18(C34H22N2=458.55) | 1-2 | m/z=508.19(C38H24N2=508.61) |
1-3 | m/z=508.19(C38H24N2=508.61) | 1-4 | m/z=534.21(C40H26N2=534.65) |
1-5 | m/z=613.23(C43H27N5=613.71) | 1-6 | m/z=613.71(C43H27N5=613.71) |
1-7 | m/z=612.23(C44H28N4=612.72) | 1-8 | m/z=612.23(C44H28N4=612.72) |
1-9 | m/z=612.23(C44H28N4=612.72) | 1-10 | m/z=689.26(C49H31N5=689.80) |
1-11 | m/z=688.26(C50H32N4=688.82) | 1-12 | m/z=688.26(C50H32N4=688.82) |
1-13 | m/z=650.25(C47H30N4=650.77) | 1-14 | m/z=574.22(C41H26N4=574.67) |
1-15 | m/z=625.25(C46H31N3=625.76) | 1-16 | m/z=534.21(C40H26N2=534.65) |
1-17 | m/z=534.21(C40H26N2=534.65) | 1-18 | m/z=625.25(C46H31N3=625.76) |
1-19 | m/z=701.28(C52H35N3=701.85) | 1-20 | m/z=610.24(C46H30N2=610.74) |
1-21 | m/z=383.13(C28H17NO=383.44) | 1-22 | m/z=433.15(C32H19NO=43350) |
1-23 | m/z=433.15(C32H19NO=43350) | 1-24 | m/z=459.16(C34H21NO=459.54) |
1-25 | m/z=538.18(C37H22N4O=538.60) | 1-26 | m/z=538.18(C37H22N4O=538.60) |
1-27 | m/z=537.18(C38H32N3O=537.61) | 1-28 | m/z=537.18(C38H32N3O=537.61) |
1-29 | m/z=537.18(C38H32N3O=537.61) | 1-30 | m/z=614.21(C43H26N4O=614.69) |
1-31 | m/z=613.22(C44H27N3O=613.70) | 1-32 | m/z=613.22(C44H27N3O=613.70) |
1-33 | m/z=575.20(C41H25N3O=575.66) | 1-34 | m/z=499.17(C35H21N3O=499.56) |
1-35 | m/z=550.20(C40H26N2O=550.65) | 1-36 | m/z=459.16(C34H21NO=459.54) |
1-37 | m/z=459.16(C34H21NO=459.54) | 1-38 | m/z=550.20(C40H26N2O=550.65) |
1-39 | m/z=626.24(C46H30N2O=626.74) | 1-40 | m/z=535.19(C40H25NO=535.63) |
2-1 | m/z=586.22(C42H26N4=586.68) | 2-2 | m/z=662.25(C48H30N4=662.78) |
2-3 | m/z=662.25(C48H30N4=662.78) | 2-4 | m/z=636.23(C46H28N4=636.74) |
2-5 | m/z=636.23(C46H28N4=636.74) | 2-6 | m/z=712.26(C52H32N4=712.84) |
2-7 | m/z=712.26(C52H32N4=712.84) | 2-8 | m/z=712.26(C52H32N4=712.84) |
2-9 | m/z=712.26(C52H32N4=712.84) | 2-10 | m/z=686.25(C50H30N4=686.80) |
2-11 | m/z=702.28(C51H34N4=702.84) | 2-12 | m/z=692.20(C48H28N4S=692.83) |
2-13 | m/z=751.27(C54H33N5=751.87) | 2-14 | m/z=676.23(C48H28N4O=676.76) |
2-15 | m/z=662.25(C48H30N4=662.78) | 2-16 | m/z=636.23(C46H28N4=636.74) |
2-17 | m/z=636.23(C46H28N4=636.74) | 2-18 | m/z=662.25(C48H30N4=662.78) |
2-19 | m/z=587.21(C41H25N5=587.67) | 2-20 | m/z=587.21(C41H25N5=587.67) |
2-21 | m/z=587.21(C41H25N5=587.67) | 2-22 | m/z=587.21(C41H25N5=587.67) |
2-23 | m/z=662.25(C48H30N4=662.78) | 2-24 | m/z=662.25(C48H30N4=662.78) |
2-25 | m/z=511.17(C36H21N3O=511.57) | 2-26 | m/z=587.20(C42H25N3O=587.67) |
2-27 | m/z=587.20(C42H25N3O=587.67) | 2-28 | m/z=561.18(C40H23N3O=561.63) |
2-29 | m/z=561.18(C40H23N3O=561.63) | 2-30 | m/z=637.22(C46H27N3O=637.73) |
2-31 | m/z=637.22(C46H27N3O=637.73) | 2-32 | m/z=637.22(C46H27N3O=637.73) |
2-33 | m/z=637.22(C46H27N3O=637.73) | 2-34 | m/z=611.20(C44H25N3O=611.69) |
2-35 | m/z=627.23(C45H29N3O=627.73) | 2-36 | m/z=617.16(C42H23N3OS=617.72) |
2-37 | m/z=676.23(C48H28N4O=676.76) | 2-38 | m/z=601.18(C42H23N3O2=601.65) |
2-39 | m/z=587.20(C42H25N3O=587.67) | 2-40 | m/z=637.22(C46H27N3O=693.73) |
2-41 | m/z=637.22(C46H27N3O=637.73) | 2-42 | m/z=587.20(C42H25N3O=587.67) |
2-43 | m/z=512.16(C35H20N4O=512.56) | 2-44 | m/z=512.16(C35H20N4O=512.56) |
2-45 | m/z=512.16(C35H20N4O=512.56) | 2-46 | m/z=512.16(C35H20N4O=512.56) |
2-47 | m/z=587.20(C42H25N3O=587.67) | 2-48 | m/z=587.20(C42H25N3O=587.67) |
有机电气元件的制造评价
[实施例1]绿色有机发光元件(发光层磷光主体)
将通过合成来得到的化合物用作发光层的发光基质材料,并根据常规方法来制造了有机电致发光元件。首先,在形成于玻璃基板的ITO层(阳极)上真空蒸镀N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine(以下简称为“2-TNATA”),来形成厚度为60nm的空穴注入层。接着,在上述空穴注入层上真空蒸镀厚度为20nm的4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(以下简称为“NPD”),来形成空穴传输层。接着,将本发明的化合物1-1作为基质材料,tris(2-phenylpyridine)-iridium(以下简称为“Ir(ppy)3”)作为掺杂物质,并以95:5的重量比进行掺杂,从而在上述空穴传输层的上部蒸镀厚度为30nm的发光层。之后,以10nm的厚度真空蒸镀双(1,1’-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(以下,简称为“BAlq”)来形成空穴阻挡层,并使tris-(8-hydroxyquinoline)aluminum(以下,简称为“Alq3”)以40nm的厚度成膜来形成电子传输层。接着,在上述电子传输层上以0.2nm的厚度蒸镀作为卤化碱金属的LiF来形成电子注入层后,以150nm的厚度蒸镀Al来形成阴极,从而制造了有机电致发光元件。
[实施例2]至[实施例40]绿色有机发光元件(发光层磷光主体)
除了使用下表4中所记载的本发明的化合物1-2至1-40作为发光层的基质材料,来代替本发明的化合物1-1之外,以与上述实施例1相同的方法制造了有机电致发光元件。
[比较例1]
除了使用下述比较化合物1作为发光层的基质材料,来代替本发明的化合物1-1之外,以与上述实施例1相同的方法制造了有机电致发光元件。
<比较化合物1>
[比较例2]
除了使用下述比较化合物2作为发光层的基质材料,来代替本发明的化合物1-1之外,以与上述实施例1相同的方法制造了有机电致发光元件。
<比较化合物2>
[比较例3]
除了使用下述比较化合物3作为发光层的基质材料,来代替本发明的化合物1-1之外,以与上述实施例1相同的方法制造了有机电致发光元件。
<比较化合物3>
向通过上述实施例1至实施例40及比较例1至比较例3制造的多个有机电致发光元件施加正向偏压直流电压,来以PhotoResearch公司(美国)的PR-650测定电发光(EL)特性,并将结果显示在下表4。此时,在300cd/m2的基准亮度下,通过Mc Science公司制造的寿命测定设备来测定了寿命T90。
【表4】
从上述表4的结果中可知,使用本发明的有机电致发光元件用材料的有机电致发光元件被用作绿色发光层材料,可实现高发光效率、低驱动电压,并可明显改善寿命。
尤其,与作为双咔唑类型的比较化合物1的CBP相比,包含五元杂环,并以五个环融合的杂环作为核心的比较化合物2、比较化合物3表现出更好的效果,而与多个比较化合物相比,再融合一个苯环来以六个环相融合的杂环形成的本发明的化合物表现出更低的驱动电压、更高的效率及更长的寿命,这可以解释为,由于还接合苯环,因而提高了热稳定性,并由于与相邻的层之间具有适当的能级,是好的能量balance带来的结果。
[实施例41]红色有机发光元件(发光层磷光主体)
将通过合成来得到的本发明的化合物用作发光层的发光基质材料,并根据常规方法来制造了有机电致发光元件。首先,在形成于玻璃基板的ITO层(阳极)上真空蒸镀2-TNATA,来形成厚度为60nm的空穴注入层。接着,在上述空穴注入层上真空蒸镀厚度为20nm的NPD,来形成空穴传输层。接着,将本发明的化合物2-1作为基质材料,将bis-(1-phenylisoquinoline)iridium(III)acetylacetonate,(以下简称为“(piq)2Ir(acac)”)作为掺杂物质,并以95:5的重量比进行掺杂,从而在上述空穴传输层的上部蒸镀厚度为30nm的发光层。之后,以10nm的厚度真空蒸镀BAlq来形成空穴阻挡层,并使Alq3以40nm的厚度成膜来形成电子传输层。接着,在上述电子传输层上以0.2nm的厚度蒸镀作为卤化碱金属的LiF来形成电子注入层后,以150nm的厚度蒸镀Al来形成阴极,从而制造了有机电致发光元件。
[实施例42]至[实施例88]红色有机发光元件(发光层磷光主体)
除了使用下表5中所记载的本发明的化合物2-2至2-48作为发光层的基质材料,来代替本发明的化合物2-1之外,以与上述实施例41相同的方法制造了有机电致发光元件。
[比较例4]
除了使用上述比较化合物1作为发光层的基质材料,来代替本发明的化合物2-1之外,以与上述实施例41相同的方法制造了有机电致发光元件。
[比较例5]
除了使用上述比较化合物2作为发光层的基质材料,来代替本发明的化合物2-1之外,以与上述实施例41相同的方法制造了有机电致发光元件。
[比较例6]
除了使用上述比较化合物3作为发光层的基质材料,来代替本发明的化合物2-1之外,以与上述实施例41相同的方法制造了有机电致发光元件。
向通过上述实施例41至实施例88及比较例4至比较例6制造的多个有机电致发光元件施加正向偏压直流电压,来以PhotoResearch公司(美国)的PR-650测定电发光(EL)特性,并将结果显示在下表5。此时,在300cd/m2的基准亮度下,通过Mc Science公司制造的寿命测定设备来测定了寿命T90。
【表5】
从上述表5的结果中可知,使用本发明的有机电致发光元件用材料的有机电致发光元件被用作红色发光层材料,可实现高发光效率、并可明显改善寿命及色纯度。
尤其,与作为双咔唑类型的比较化合物1的CBP相比,包含五元杂环,并以五个环融合的杂环作为核心的比较化合物2、比较化合物3表现出更好的效果,而再融合一个苯环来以六个环相融合的杂环上取代有多个喹唑啉衍生物的本发明的化合物作为红色主体,表现出最优秀的结果。其中的原因可与对绿色发光层元件的结果中说明的理由相同。
本发明的多个化合物即使用于有机电致发光元件的其他有机物层如空穴注入层、空穴传输层、电子注入层、电子传输层也可获得相同的效果,这是不言而喻的。
以上的说明仅为例示,只要是本发明所属技术领域的普通技术人员,就能在不脱离本发明的本质特性的范围内进行多种变形。因此,本说明书所公开的实施例并不用于限定本发明,而是用于说明本发明,本发明的思想和范围不会因这种实施例而受到限制。本发明的保护范围应根据发明要求保护范围来解释,与其等同范围内的所有技术应解释为包括在本发明的保护范围。
附图标记的说明
100:有机电气元件 110:基板
120:第一电极 130:空穴注入层
140:空穴输送层 141:缓冲层
150:发光层 151:发光辅助层
160:电子输送层 170:电子注入层
180:第二电极
相关专利申请的交叉引用
本专利申请根据美国专利法119(a)条(35 U.S.C§119(a)),针对2013年03月15日在韩国申请的专利申请编号第10-2013-0027621号主张优先权,其全部内容作为参照文献合并于本专利申请。并且,除了在美国之外,若本专利申请在其他国家也以相同的理由而主张优先权,则其全部内容作为参照文献合并于本专利申请。
Claims (8)
1.一种化合物,其特征在于,由以下化学式1表示,
化学式1:
在上述化学式中,
m、n及o分别为1~4的整数,
R1至R3能够相互独立地选自由氢、重氢、超重氢、C6的芳基及-L1-N(Ar2)(Ar3)组成的组,
X为O,
Ar1选自由C6-C20的芳基、包含O、N及S中的至少一种杂原子的C2-C20的杂环基及-L1-N(Ar2)(Ar3)组成的组,上述芳基及杂环基能够分别被选自由重氢、C6-C20的芳基、被重氢取代的C6-C20的芳基、及包含O、N及S中的至少一种杂原子的C2-C20的杂环基组成的组中的一种以上取代基来取代,
Ar2及Ar3分别是C6的芳基,
上述L1是单键或C6的亚芳香基。
2.一种化合物,其特征在于,由以下化学式中的一个表示,
上述化学式3和化学式4中,m、n及o分别为1~4的整数,
R1至R3能够相互独立地选自由氢、重氢及C6的芳基组成的组,
其中,R4是C6-C12的芳基,
Ar4选自由C6-C20的芳基、包含O、N及S中的至少一种杂原子的C2-C20的杂环基及芴基组成的组,
Z1至Z4分别独立地表示CR5或N,其中,R5是氢或C6-C10的芳基。
3.一种化合物,其特征在于,由以下化学式表示,
4.一种有机电气元件,其特征在于,包括第一电极、第二电极、以及位于上述第一电极和第二电极之间的有机物层,
其中,上述有机物层含有权利要求1-3所述的化合物。
5.根据权利要求4所述的有机电气元件,其特征在于,借助溶解工序将上述化合物形成为上述有机物层。
6.根据权利要求4所述的有机电气元件,其特征在于,
上述有机物层包括发光层,
上述化合物被用作上述发光层的基质材料。
7.一种电子装置,其特征在于,包括:
显示装置,包括权利要求4的有机电气元件;以及
控制部,用于驱动上述显示装置。
8.根据权利要求7所述的电子装置,其特征在于,上述有机电气元件为有机电致发光元件、有机太阳能电池、有机感光体、有机晶体管及单色照明用元件中的至少一个。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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KR1020130027621A KR102081689B1 (ko) | 2013-03-15 | 2013-03-15 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR10-2013-0027621 | 2013-03-15 | ||
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JP6343334B2 (ja) | 2018-06-13 |
KR102081689B1 (ko) | 2020-02-26 |
US20160020410A1 (en) | 2016-01-21 |
JP2017071640A (ja) | 2017-04-13 |
JP6091664B2 (ja) | 2017-03-08 |
JP2018083836A (ja) | 2018-05-31 |
WO2014142472A1 (ko) | 2014-09-18 |
US9799835B2 (en) | 2017-10-24 |
CN105102460A (zh) | 2015-11-25 |
JP2016512495A (ja) | 2016-04-28 |
KR20140112924A (ko) | 2014-09-24 |
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