CN112812108B - 化合物及包含该化合物的有机电致发光装置 - Google Patents
化合物及包含该化合物的有机电致发光装置 Download PDFInfo
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- CN112812108B CN112812108B CN201911121181.2A CN201911121181A CN112812108B CN 112812108 B CN112812108 B CN 112812108B CN 201911121181 A CN201911121181 A CN 201911121181A CN 112812108 B CN112812108 B CN 112812108B
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- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
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- 229960005323 phenoxyethanol Drugs 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 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
- 239000008096 xylene Substances 0.000 description 1
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Abstract
本发明涉及化合物、包含该化合物的有机电致发光装置。本发明化合物的结构式如下式I所示,该化合物可用作制备有机电致发光装置,该化合物能够改善有机溶解度和稳定性,降低升华提纯的温度,通过使用该化合物,可以提高元件的效率和寿命。
Description
技术领域
本发明涉及有机电致发光技术领域。具体地,涉及一种化合物和包含该化合物的有机电致发光装置。
背景技术
有机电致发光元件所使用的物质大部分为纯有机物或有机物与金属形成络合物的有机金属络合物,根据用途可区分为空穴注入物、空穴输送物、发光物、电子输送物、电子注入物等。在此,作为空穴注入物或空穴输送物主要使用离子化能相对较小的有机物,作为电子注入物或电子输送物主要使用电负性较大的有机物。此外,作为发光辅助层所使用的物质最好能满足如下特性。
第一、有机电致发光元件中所使用的物质需较好的热稳定性,其原因是在有机电致发光元件内部因电荷的迁移而产生焦耳热。目前,作为空穴输送层通常所使用的材料需要具有低玻璃化温度,以避免在低温下驱动时出现因发生结晶化而引起发光效率降低的现象。第二、为了降低驱动电压,需要与阴极和阳极邻接的有机物具有小的电荷注入势垒和高的电荷迁移率。第三、由于电极和有机层的界面、有机层和有机层的界面上一直存在能量壁垒而不可避免地累积电荷,因此有机电致发光元件中所使用的物质需要具有优异的电化学稳定性。
发光层由主发光体和掺杂物这两种物质构成,掺杂物需要量子效率高,与掺杂物相比主发光体需要能隙大而容易发生向掺杂物的能量转移。用于电视、移动设备等的显示器根据红色、绿色、蓝色这三原色实现全彩色,发光层分别由红色主发光体/掺杂物、绿色主发光体/掺杂物以及蓝色主发光体/掺杂物构成。目前蓝光材料仍然存在发光量子效率低、色纯度差的问题。造成这种状况的主要原因是因为蓝光来自于能隙较宽的能级间的跃迁,而宽禁带的有机化合物在进行分子设计时存在一定的困难,其次蓝光材料的体系中存在着较强的π-π键相互作用,有着很强的电荷转移特性,从而使宽带隙中存在更多的无辐射弛豫通道,加剧了分子之间荧光淬灭,降低了蓝光体系的量子产率。现有工序中由于化合物在溶液中的溶解度不,因此需要使用蒸镀工序制造有机发光器件中的蓝光掺杂物,该蒸镀工序的生产性较差且花费较大。
因此设计合成综合性能优良的蓝光材料,是有机电致发光材料研究的重要课题。
发明内容
为解决现有技术中发光材料较难发出蓝光、且发光效率低、热稳定性差、电荷注入势垒高、电荷迁移率低、电化学稳定性差的问题,
本发明提供一种新型的有机化合物,该有机化合物在芘分子两侧引入两个戊环、增大分子内共轭效应和空间位阻的同时,阻碍有机分子间激-激复合物的生成、增加内部电子密度和稳定性,提高有机化合物的稳定性和在有机溶媒中的溶解性,使有机化合物在低温下也可以进行升华、蒸镀以及进行溶液工序,并且与以住的化合物相比具有更短的发光波长,从而提高器件的效率、寿命,由此解决上述现有技术中存在的问题。
本发明的目的还在于提供利用上述有机化合物的有机电致发光装置。
本发明还提供上述有机化合物在有机电致发光装置中和有机电致发光材料中的应用
为达到上述目的,本发明采用下述技术方案:
具体地,本发明提供一种化合物,其结构如式I所示:
式I中,R1、R2、R3、R4、R5、R6、R7、R8、Ra、Rb各自独立地选自氢、氘、C1~C40直链烷基或C3~C40支链或环烷基组成的组,其中,任意相邻的取代基之间任选接合形成环状化合物,任意一个或多个氢原子任选被基团R取代;
Ar1、Ar2、Ar3、Ar4各自独立地选自C5~C60芳香族环系或杂芳族环系组成的组,其中,任意一个或多个氢原子任选被氟原子取代,且Ar1和Ar2、Ar3和Ar4可通过单键、O、S、SO、SO2、C(R)2、NR作为桥连基彼此桥连形成环;
表示单键或双键;
所述基团R各自独立地选自氘原子、卤素原子、腈基、C1~C40直链烷基、C1~C40直链杂烷基、C3~C40支链或环烷基、C3~C40支链或环杂烷基、C2~C40烯基或炔基、C5~C80芳族环或杂芳族环系组成的组;
其中两个或多个相邻的取代基R任选接合或稠合形成单环或多环的脂肪环化合物、芳族环系或杂芳族环系。
本发明还提供一种有机电致发光装置,该装置包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个有机层,所述有机层包含本发明提供的有机化合物中的一种或多种。
本发明还提供一种化合物在制备有机电致发光装置中的应用。
本发明还提供一种化合物在制备有机电致发光材料中的应用。
本发明的有益效果:
本发明提供的新型化合物,是一系列具有戊并芘环结构的新型有机电致发光材料,通过在芘分子的外侧引入两个大位阻的取代基以及戊基团,增大芘分子的共轭面积和空间位阻,阻碍由于分子间的π-π共轭作用生成激发态复合物,改善分子的有机溶解度和稳定性,使化合物在溶液中的溶解度提高,从而能够使用溶液工序制备有机发光器件中的蓝光掺杂物,改善原有蒸镀工序的生产性较差且花费较大的问题。同时该新型化合物能够降低升华提纯的温度,提高元件的效率和寿命。该新型化合物发光为深蓝色且发光效率高,同时具有较好的热稳定性、小的电荷注入势垒、高的电荷迁移率和优异的电化学稳定性的优点。
具体实施方式
[有机电致发光化合物]
一种化合物,其结构如式I所示:
式I中,R1、R2、R3、R4、R5、R6、R7、R8、Ra、Rb各自独立地选自氢、氘、C1~C40直链烷基或C3~C40支链或环烷基组成的组,其中,任意相邻的取代基之间任选接合形成环状化合物,任意一个或多个氢原子任选被基团R取代;
Ar1、Ar2、Ar3、Ar4各自独立地选自C5~C60芳香族环系或杂芳族环系组成的组,其中,任意一个或多个氢原子任选被氟原子取代,且Ar1和Ar2、Ar3和Ar4可通过单键、O、S、SO、SO2、C(R)2、NR作为桥连基彼此桥连形成环;
表示单键或双键;
所述基团R各自独立地选自氘原子、卤素原子、腈基、C1~C40直链烷基、C1~C40直链杂烷基、C3~C40支链或环烷基、C3~C40支链或环杂烷基、C2~C40烯基或炔基、C5~C80芳族环或杂芳族环系组成的组;
其中两个或多个相邻的取代基R任选接合或稠合形成单环或多环的脂肪环化合物、芳族环系或杂芳族环系。
优选地,所述表示单键。。
优选地,所述R1、所述R2、所述R3、所述R4、所述R5、所述R6、所述R7、所述R8、所述Ra、所述Rb各自独立地选自氢、氘、C1~C40链烷基、C3~C40、环烷基组成的组,其中任意相邻的取代基之间任选接合形成环状化合物,但任意氢原子不被基团R取代。
优选地,所述R1、所述R2、所述R3、所述R4、所述R5、所述R6、所述R7、所述R8、所述Ra、所述Rb各自独立地选自氢、氘、C1~C40链烷基、C3~C40、环烷基组成的组,其中,任意相邻的取代基之间不接合形成环状化合物,任意氢原子不能被基团R取代。
本发明意义上的芳基含有6~60个碳原子,在本发明意义上的杂芳基含有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。此处的芳基或杂芳基被认为是指简单的芳族环,即苯、萘等,或简单的杂芳族环,如吡啶、嘧啶、噻吩等,或稠合的芳基或杂芳基,如蒽、菲、喹啉、异喹啉等。通过单键彼此连接的芳族环,例如联苯,相反地不被称为芳基或杂芳基,而是称为芳族环系。
在本发明意义上的芳族或杂芳族环系旨在被认为是指不必仅含有芳基或杂芳基的体系,而是其中多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接。因此,例如,和其中两个或更多个芳基被例如短的烷基连接的体系一样,诸如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的体系也被认为是指在本发明意义上的芳族环系。
对于本发明意义上的含有1~40个碳原子并且其中单独的氢原子或-CH2-基团还可被上述基团取代的脂族烃基或者烷基或者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-基团可被氧、硫、卤素原子取代的基团,被认为是指烷氧基、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。
根据本发明的芳族或杂芳族环原子,特别是指衍生自如下物质的基团:苯、萘、蒽、苯并蒽、菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘,4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。
本发明的化合物中,优选选自下述的式SLC-B421~SLC-B603所示的化合物组成的组,其中Z为-O-或-S-:
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[有机电致发光装置]
本发明还提供一种有机电致发光装置,其包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个有机层,所述有机层包含本发明的有机化合物中的一种或多种。
优选地,所述有机层还包括电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层中的一种或多种以及发光层。
优选地,所述发光层包括主发光体和掺杂物,所述主发光体选自萘、蒽、芘、苝、菲、荧蒽、苯并蒽和并五苯及其衍生物组成的组、所述掺杂物包含本发明的有机化合物中的一种或多种。
[有机电致发光化合物的应用]
本发明的保护范围还包括上述化合物在有机电致发光装置中的应用。
本发明的保护范围还包括上述化合物在有机电致发光材料中的应用。有机发光器件用材料可以单独使用本发明的化合物构成,也可以同时含有其他化合物。
本发明的有机电致发光器件用材料中所含有的本发明的化合物可以用作但不限于空穴注入材料、空穴传输材料或荧光发光材料。
所述有机电致发光器件包含阴极、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。
在本发明的另一个实施方式中,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,如在对比文件WO2005053051中所述的。
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器件,其特征在于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器件,其特征在于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,其特征在于从溶液中,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,其特征在于借助于升华方法来施加至少一个层,和/或特征在于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/或特征在于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。从液相处理根据本发明的化合物,例如通过旋涂或通过印刷方法进行处理,需要根据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。
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。
附图说明
下面结合附图对本发明的具体实施方式作进一步详细的说明。
图1中示出本发明的有机电致发光装置的一个底部发光例子的示意图。
图2中示出本发明的有机电致发光装置的一个顶部发光例子的示意图。
图1、图2中,有机电致发光装置具有基板1、阳极2、阴极8,以及配置于阳极2与阴极8之间的层3~7。其中,在阴极8与发光层5之间配置有空穴阻挡/电子传输层6和电子注入层7,在发光层5与阳极2之间配置有空穴注入3和空穴传输/电子阻挡层4。
本发明的有机电致发光器件中,上述的本发明的化合物优选包含在发光层5中。
具体实施方式
为了更清楚地说明本发明,下面结合优选实施例和附图对本发明做进一步的说明。本领域技术人员应当理解,下面所具体描述的内容是说明性的而非限制性的,不应以此限制本发明的保护范围。
本发明中,制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得,所述百分比如无特殊说明均为质量百分比。本发明提供的一系列新型有机化合物,所有的反应都是在众所周知的适合条件下进行,有些涉及到简单的有机制备,例如苯硼酸衍生物的制备均能通过熟练的操作技能合成,在本发明中没有详细描述。
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;
寿命测试:使用LTS-1004AC寿命测试装置。
实施例1
化合物SLC-B421的制备:
将4.2g(10.0mmol)的4,9-二溴-1,2,6,7-四氢双环戊基[cd,jk]芘分散在80ml的甲苯中,加入24.0mmol的N-(4-异丙基苯基)二苯并[b,d]呋喃-4-胺或N-(4-异丙基苯基)二苯并[b,d]噻吩-4-胺,再加入2.4g(25.0mmol)的叔丁醇钠、45.8mg(0.05mmol)的Pd2(dba)3催化剂和0.05ml的10%叔丁基磷甲苯溶液,升温至100℃搅拌反应12小时,反应结束后,加入50ml的水,分出有机相,水相用甲苯萃取,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,获得SLC-B421,黄色固体。MS(MALDI-TOF):m/z Z=O,852.3702[M+],Z=S,884.3225[M+]。
实施例2
化合物SLC-B445的制备方法,包括如下步骤:
第一步:化合物Int-1的制备
在氮气保护下,2.55g(10.0mmol)的1,2,6,7-四氢双戊基[cd,jk]芘溶于100ml干燥的二氯甲烷中,加入0.12g(0.9mmol)的无水氯化铝,用冰水浴降温至0℃,缓慢滴加入2.0g的叔丁基氯溶于15ml的二氯甲烷溶液,搅拌反应半小时,升到室温搅拌反应12小时,滴加入20ml的2N稀盐酸水溶液,搅拌反应1小时,分出有机相,水相用二氯甲烷萃取,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到白色固体,收率94%。
第二步:化合物Int-2的制备
将上步制备的5.4g(14.7mmol)化合物Int-1溶解在120ml的氯仿中,加入5.8g(32.4mmol)的NBS,室温搅拌反应12小时,反应结束后,加入50ml的饱和亚硫酸氢钠水溶液,分出有机相,有机相用水洗三次,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到5.5g的Int-2,白色固体,收率72%。
第三步:化合物SLC-B445的制备:
将5.2g(10.0mmol)的4,9-二溴-3,8-二叔丁基-1,2,6,7-四氢双环戊基[cd,jk]芘分散在80ml的甲苯中,加入24.0mmol的N-苯基-二苯并[b,d]呋喃-4-胺或N-苯基-二苯并[b,d]噻吩-4-胺,再加入2.4g(25.0mmol)的叔丁醇钠、45.8mg(0.05mmol)的Pd2(dba)3催化剂和0.05ml的10%叔丁基磷甲苯溶液,升温至100℃搅拌反应12小时,反应结束后,加入50ml的水,分出有机相,水相用甲苯萃取,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,获得SLC-B445,黄色固体。MS(MALDI-TOF):m/z Z=O,880.4006[M+],Z=S,912.3545[M+]。
实施例3
化合物SLC-B422~SLC-B444、SLC-B446~SLC-B507的制备:
参照实施例1和实施例2的制备方法,将实施例1中的N-(4-异丙基苯基)二苯并[b,d]呋喃-4-胺或N-(4-异丙基苯基)二苯并[b,d]噻吩-4-胺替换为相应取代的芳胺,或将实施例2中第三步的N-苯基-二苯并[b,d]呋喃-4-胺或N-苯基-二苯并[b,d]噻吩-4-胺替换为相应取代的芳胺,制备目标化合物SLC-B422~SLC-B444、SLC-B446~SLC-B507,下表1列出制备获得的目标化合物的结构确证结果:
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实施例4
化合物SLC-B510的制备方法,包括如下步骤:
第一步:化合物Int-3的制备
5.2g(10.0mmol)的4,9-二溴-3,8-二叔丁基-1,2,6,7-四氢双环戊基[cd,jk]芘溶解在150ml的二甲苯中,加入5.2g的氧化锰,升温至120℃搅拌反应12小时,再加入5.2g的氧化锰,继续反应12小时,结束后,冷却到室温,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到4.3g的Int-3,黄色固体,收率84%。
第二步:化合物SLC-B510的制备:
参照实施例2第三步的制备方法,将实施例2第三步的4,9-二溴-3,8-二叔丁基-1,2,6,7-四氢双环戊基[cd,jk]芘替换为4,9-二溴-3,8-二叔丁基双环戊基[cd,jk]芘,用硅胶柱分离纯化,获得SLC-B510,黄色固体。MS(MALDI-TOF):m/z Z=O,877.3821[M+H]+,Z=S,909.3365[M+H]+。
实施例5
化合物SLC-B508、SLC-B509、SLC-B511~SLC-B549的制备:
参照实施例4的制备方法,将实施例4第一步中的4,9-二溴-3,8-二叔丁基-1,2,6,7-四氢双环戊基[cd,jk]芘替换为4,9-二溴-1,2,6,7-四氢双环戊基[cd,jk]芘,将实施例4第二步中的N-苯基-二苯并[b,d]呋喃-4-胺或N-苯基-二苯并[b,d]噻吩-4-胺替换为相应取代的二芳胺制备目标化合物SLC-B508、SLC-B509、SLC-B511~SLC-B549,下表2列出制备获得的目标化合物的结构确证结果:
实施例6
化合物SLC-B591的制备:
将4.7g(10.0mmol)的4,9-二溴-1,1,7,7-四甲基-1,2,6,7-四氢双环戊基[cd,jk]芘分散在80ml的甲苯中,加入24.0mmol的N-苯基-二苯并[b,d]呋喃-4-胺或N-苯基-二苯并[b,d]噻吩-4-胺,再加入2.4g(25.0mmol)的叔丁醇钠、45.8mg(0.05mmol)的Pd2(dba)3催化剂和0.05ml的10%叔丁基磷甲苯溶液,升温至100℃搅拌反应12小时,反应结束后,加入50ml的水,分出有机相,水相用二氯甲烷萃取,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,获得SLC-B591,黄色固体。MS(MALDI-TOF):m/z Z=O,824.3368[M+],Z=S,856.2907[M+]。
实施例7
化合物SLC-B550~SLC-B590、SLC-B592~SLC-B603的制备:
参照实施例6的制备方法,将实施例6中的N-苯基-二苯并[b,d]呋喃-4-胺或N-苯基-二苯并[b,d]噻吩-4-胺替换为相应取代的芳胺制备目标化合物SLC-B550~SLC-B590、SLC-B592~SLC-B603,下表3列出制备获得的目标化合物的结构确证结果:
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实施例8
一种OLED元件,如图1所示,包括基板1、设于基板1上的阳极层2、设于阳极层2上的空穴注入层3、设于空穴注入层3上的空穴传输层4、设于空穴传输层4上的电子阻挡层5、设于电子阻挡层5上的有机发光层6、设于有机发光层6上的空穴阻挡层7、设于空穴阻挡层7上的电子传输层8、设于电子传输层8上的阴极层9。
上述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,在上述阳极层膜上继续分别蒸镀化合物DNTPD作为空穴注入层,蒸镀膜厚为在上述空穴注入层膜上继续蒸镀NPB为空穴传输层,蒸镀膜厚为/>
3)在空穴传输层上继续蒸镀一层化合物QIFA作为电子阻挡层,其蒸镀蒸镀膜厚为
4)在电子阻挡层上继续蒸镀一层本发明的化合物式I和ADN作为有机发光层,其中,ADN为主体材料和本发明的化合物式I为掺杂材料,化合物式I在ADN中的掺杂浓度为5%,蒸镀膜厚为
5)在上述有机发光层上再继续蒸镀一层化合物TPBI作为空穴阻挡层,蒸镀膜厚为
6)在上述空穴阻挡层上再继续蒸镀一层化合物LiF作为器件的电子传输层,蒸镀膜厚为最后,在上述电子传输层之上蒸镀金属铝作为元件的阴极层,蒸镀膜厚为
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B421,得到本发明提供的元件EL-1;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B435,得到本发明提供的元件EL-2;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B445,得到本发明提供的元件EL-3;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B459,得到本发明提供的元件EL-4;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B467,得到本发明提供的元件EL-5;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B510,得到本发明提供的元件EL-6;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B557,得到本发明提供的元件EL-7;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B581,得到本发明提供的元件EL-8;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物SLC-B591,得到本发明提供的元件EL-9;
按照与上相同的步骤,仅将步骤4)所用化合物式I替换为化合物BD01,得到对比元件EL-10;
所得元件EL-1至EL-10的性能检测结果如表4所示:
表4性能检测结果
上述实施例8中使用的化合物结构如下:
从性能测试结果表4可以看到,本发明的化合物作为蓝光掺杂材料相较于采用BD01作为蓝光掺杂材料的有机电致发光器件,外量子效率和寿命均有较大提高,而且器件电流密度在10mA/cm2的条件下,驱动电压降低到5.0V以下。
产业上的应用可能性
本发明的有机电致发光元件可以在壁挂电视、平板显示器、照明等的平面发光体、复印机、打印机、液晶显示器的背光源或计量仪器类等的光源,显示板、标识灯等中应用。
显然,本发明的上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定,对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动,这里无法对所有的实施方式予以穷举,凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。
Claims (4)
1.一种化合物,其结构选自下述所示的化合物组成的组:
,
其中Z表示O或S。
2.一种有机电致发光装置,其特征在于,所述有机电致发光装置包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个有机层,所述有机层包括:电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层中的一种或多种以及发光层;
所述发光层包括主发光体和掺杂物,所述主发光体选自萘、蒽、芘、苝、菲、荧蒽、苯并蒽和并五苯及其衍生物组成的组、所述掺杂物包含权利要求1所述的有机化合物中的一种或多种。
3.一种权利要求1所述化合物作为掺杂物在制备有机电致发光装置中的应用。
4.一种权利要求1所述化合物作为掺杂物在制备有机电致发光材料中的应用。
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