CN106008424A - 用于有机电致发光装置的材料和有机电致发光装置 - Google Patents
用于有机电致发光装置的材料和有机电致发光装置 Download PDFInfo
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- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
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Abstract
本公开的多个实施方式涉及用于有机电致发光装置的材料(由式1表示)以及使用该材料的装置:式1Ar1和Ar2可以是具有6至30个碳原子的取代的或者未取代的芳基或者具有5至30个碳原子的取代的或者未取代的杂芳基,Ar3可以是如上所述的取代的或者未取代的芳基或者杂芳基或者具有1至6个碳原子的烷基,HAr可以是具有5至30个碳原子的取代的或者未取代的杂芳基,L可以选自直接连接、具有6至30个碳原子的取代的或者未取代的亚芳基和具有5至30个碳原子的取代的或者未取代的亚杂芳基,并且HAr和Ar3可以彼此不同。
Description
相关申请的交叉引用
本申请要求于2015年3月31日在日本专利局提交的日本专利申请第2015-070934号的优先权和权益,其全部内容通过引用并入本文。
技术领域
本公开的实施方式的一个或多个方面涉及用于有机电致发光装置的材料,以及包括该材料的有机电致发光装置。
背景技术
当前正积极地开发有机电致发光(EL)显示器。不同于液晶显示器等等,有机EL显示器是所谓的自发光显示器,其通过在发光层中复合来自阳极和阴极的空穴和电子以产生激子来运行。通过发光层中的发光有机化合物发出光。
实例有机EL装置包括阳极、阳极上的空穴传输层、空穴传输层上的发光层、发光层上的电子传输层和电子传输层上的阴极。由阳极注入的空穴经由空穴传输层移动至发光层。由阴极注入的电子经由电子传输层移动至发光层。当注入发光层中的空穴和电子复合时,在发光层中产生激子。有机EL装置使用由激子的辐射衰减生成的能量发光。有机EL装置的配置不限于以上实例,并且可多样地变化。
当有机EL装置用于显示仪器中时,有机EL装置必须展示高的发光效率和长的寿命(例如,使用期限)。然而,在许多有机EL装置中,驱动电压高并且发光效率和寿命不足,例如,在蓝光发光区域中的那些。提高空穴传输层的标准化和稳定性的方法已被考察作为提高有机EL装置的效率和寿命的策略。
许多芳香胺化合物可供用作用于空穴传输层中的空穴传输材料。例如,用杂芳环在芴基的9位处取代的一元胺衍生物已被建议作为有用的材料,用于提高有机EL装置的寿命。然而,仍有与解决装置的发光效率和寿命相关的问题,并且难以声称使用该材料的有机EL装置具有足够的寿命。
因此,需要进一步开发用于具有长寿命的有机EL装置的材料以及使用该材料的有机EL装置。
发明内容
本公开的实施方式的一个或者多个方面涉及用于具有长寿命的有机EL装置的材料,和使用该材料的有机EL装置。
本公开的一个或者多个实施方式涉及用于有机电致发光装置的材料和使用该材料的有机电致发光装置,并且涉及用于具有高发光效率和长寿命的有机电致发光装置的材料,和使用该材料的有机电致发光装置。
本公开的一个实施方式提供了用于具有长寿命的有机EL装置的材料,和在发光层和阳极之间的至少一个层压层中使用该材料的有机EL装置。
本公开的一个实施方式提供了由以下式1表示的用于有机EL装置的材料:
式1
在式1中,Ar1和Ar2可以各自独立地选自具有6至30个用于形成环的碳原子的取代的或者未取代的芳基和具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基,Ar3可以选自具有6至30个用于形成环的碳原子的取代的或者未取代的芳基、具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基和具有1至6个碳原子的烷基,HAr可以是具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基,L可以选自直接连接、具有6至30个用于形成环的碳原子的取代的或者未取代的亚芳基和具有5至30个用于形成环的碳原子的取代的或者未取代的亚杂芳基,并且HAr和Ar3可以彼此不同。
在一个实施方式中,Ar1至Ar3可以各自独立地为具有6至30个用于形成环的碳原子的取代的或者未取代的芳基。
在一个实施方式中,HAr可以选自二苯并呋喃基和二苯并噻吩基。
根据本公开的实施方式的用于有机EL装置的材料可以在芴基的9位处包括杂芳基和不同于该杂芳基的取代基,并且将芴基与胺结合或者连接,使得整个分子大体上是非对称的,并且材料可以是更加无定形的(amorphous)。因此,电荷传输可以变得顺畅(例如,可被改善),并且有机EL装置的寿命可被改善。
在本公开的一个实施方式中,有机EL装置在至少一层中包括该用于有机EL装置的材料。
根据本公开的一个实施方式的有机EL装置在至少一层中包括该用于有机EL装置的材料,并且有机EL装置可以实现长的寿命。
在本公开的一个实施方式中,有机EL装置在发光层和阳极之间的至少一个层压层中包括该用于有机EL装置的材料。
根据本公开的一个实施方式的有机EL装置在发光层和阳极之间的至少一个层压层中包括该用于有机EL装置的材料,并且有机EL装置可以实现长的寿命。
根据本公开的一个实施方式的有机EL装置在空穴传输层中包括该用于有机EL装置的材料,并且有机EL装置可以实现长的寿命。
附图说明
本文包括附图以便本公开能够进一步理解,附图并入该说明书并且组成该说明书的一部分。附图图解了本公开的实例实施方式,并且连同说明书一起,用于解释本公开的原理。在附图中:
图1是示出根据本公开的一个实施方式的有机EL装置的示意图;以及
图2是示出根据本公开的另一实施方式的有机EL装置的示意图。
具体实施方式
下文中,将参考附图描述根据本公开的实施方式的用于有机EL装置的材料和包括该材料的有机EL装置。然而,用于有机EL装置的材料和包括该材料的有机EL装置可以以不同的形式进行实施,并且不被解释为限于本文阐述的实施方式。在图中,相同的附图标记自始至终指代相同的元件或者具有相同功能的元件,并且将不提供其重复的解释。
为了清楚,在图中可能夸大层、膜、板、区域等等的厚度。将理解的是当元件,比如层、膜、区域或者基板被称为“在”另一元件“上”时,其可以直接在另一元件上或者也可能存在中间的元件。相比之下,当元件被称为“直接在”另一元件“上”时,则不存在中间的元件。
根据本公开的一个实施方式的用于有机EL装置的材料可以是由以下式1表示的胺化合物:
式1
在式1中,Ar1和Ar2可以各自独立地选自具有6至30个用于形成环的碳原子的取代的或者未取代的芳基和具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基,并且Ar3可以选自具有6至30个用于形成环的碳原子的取代的或者未取代的芳基、具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基和具有1至6个碳原子的烷基。HAr可以是具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基。L可以选自直接连接、具有6至30个用于形成环的碳原子的取代的或者未取代的亚芳基和具有5至30个碳原子的取代的或者未取代的亚杂芳基。如本文所使用的,“用于形成环的原子”可以指代“成环原子”。如本文所使用的,“直接连接”可以指代键,比如单键。
在式1中,用作Ar1和Ar2的具有6至30个用于形成环的碳原子的芳基的非限制性实例可以包括苯基、萘基、蒽基、菲基、联苯基、三联苯基、四联苯基、芴基、亚三苯基、亚联苯基、芘基、苯并荧蒽基、屈基、苯基萘基、萘基苯基,等等。在一些实施方式中,可以包括萘基、联苯基、苯基萘基和萘基苯基。
用作Ar1和Ar2的具有5至30个用于形成环的碳原子的杂芳基的非限制性实例可以包括吡啶基、喹啉基、异喹啉基、苯并呋喃基、苯并噻吩基、吲哚基、苯并噁唑基、苯并噻唑基、喹喔啉基、苯并咪唑基、二苯并呋喃基、二苯并噻吩基、咔唑基,等等。
在式1中,用作Ar3的具有6至30个用于形成环的碳原子的芳基和具有5至30个用于形成环的碳原子的杂芳基的非限制性实例可以与用作以上的Ar1和Ar2的那些相同。
用作Ar3的具有1至6个碳原子的取代或未取代的烷基的非限制性实例可以包括甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、正己基、羟甲基、1-羟乙基、2-羟乙基、2-羟基异丁基、1,2-二羟基乙基、1,3-二羟基异丙基、2,3-二羟基-叔丁基、1,2,3-三羟基丙基、氯甲基、1-氯乙基、2-氯乙基、2-氯异丁基、1,2-二氯乙基、1,3-二氯异丙基、2,3-二氯-叔丁基、1,2,3-三氯丙基、溴甲基、1-溴乙基、2-溴乙基、2-溴异丁基、1,2-二溴乙基、1,3-二溴异丙基、2,3-二溴-叔丁基、1,2,3-三溴丙基、碘甲基、1-碘乙基、2-碘乙基、2-碘异丁基、1,2-二碘乙基、1,3-二碘异丙基、2,3-二碘-叔丁基、1,2,3-三碘丙基、氰甲基、1-氰基乙基、2-氰基乙基、2-氰基异丁基、1,2-二氰基乙基、1,3-二氰基异丙基、2,3-二氰基-叔丁基、1,2,3-三氰基丙基、硝基甲基、1-硝基乙基、2-硝基乙基、2-硝基异丁基、1,2-二硝基乙基、1,3-二硝基异丙基、2,3-二硝基-叔丁基、1,2,3-三硝基丙基、环丙基、环丁基、环戊基、环己基、4-甲基环己基,等等。
在一些实施方式中,Ar1至Ar3可以选自取代的或者未取代的芳基、取代的或者未取代的苯基、萘基、萘基苯基、苯基萘基和联苯基。
在一些实施方式中,在式1中,用作HAr的具有5至30个用于形成环的碳原子的杂芳基可以与以上用于Ar1和Ar2的那些相同。在一些实施方式中,HAr可以选自取代的或者未取代的二苯并呋喃基或者二苯并噻吩基。如上所述,HAr可以是与Ar3不同的取代基。
在式1中,用作L的具有6至30个用于形成环的碳原子的亚芳基和具有5至30个用于形成环的碳原子的亚杂芳基的非限制性实例可以包括亚苯基、亚联苯基、亚三联苯基、亚萘基、亚蒽基、亚菲基、亚芴基、亚茚基、亚芘基、乙酰基亚萘基、荧蒽基、三亚苯基、亚吡啶基、亚吡喃基、亚喹啉基、亚异喹啉基、亚苯并呋喃基、亚苯并噻吩基、亚吲哚基、咔唑基、亚苯并噁唑基、亚苯并噻唑基、喹喔啉基、亚苯并咪唑基、亚吡唑基、亚二苯并呋喃基、亚二苯并噻吩基,等等。
在式1中,在其中Ar1至Ar2、HAr和L具有取代基的情况中,其取代基可以选自烷基(比如甲基、乙基、丙基、戊基和己基)和芳基(比如苯基、联苯基和萘基)。在其中Ar3具有取代基的情况中,其取代基可以选自烷基(比如甲基、乙基、丙基、戊基和己基)、芳基(比如苯基、联苯基和萘基)、羟基、卤素、氰基、硝基等。Ar1至Ar3和HAr可以用多个取代基取代。该多个取代基可以结合(例如,连接)以形成饱和的或者不饱和的环。
根据本公开的一个实施方式,由式1表示的胺化合物作为用于有机EL装置的材料可以在芴基的9位处包括杂芳基HAr和与杂芳基不同的取代基Ar3,芴基与胺部分结合或者连接,使得整个分子大体上是非对称的,并且材料可以是更加无定形的。因此,电荷传输可以变得顺畅(例如,可被改善),并且有机EL装置的寿命可被改善。
根据本公开的一个实施方式,由式1表示的用于有机EL装置的材料可非限制性地地由选自以下化合物1至138的一个表示。
根据本公开的实施方式的用于有机EL装置的材料可被包括在选自形成有机EL装置的多个有机层的至少一层中。在一些实施方式中,材料可被包括在有机EL装置中的发光层和阳极之间的至少一个层压层中。
如上所述,根据本公开的实施方式的用于有机EL装置的材料可以在芴基的9位处包括杂芳基HAr和与该杂芳基不同的取代基Ar3,芴基与胺结合或者连接,使得整个分子大体上是非对称的,并且材料可以是更加无定形的。因此,电荷传输可以变得顺畅(例如,可被改善),并且有机EL装置的寿命可被改善。
有机EL装置
下文中,将说明根据本公开的实施方式的使用用于有机EL装置的材料的有机EL装置。图1是图解根据本公开的实施方式的有机EL装置100的示意图。有机EL装置100可以包括,例如基板102、阳极104、空穴注入层106、空穴传输层108、发光层110、电子传输层112、电子注入层114和阴极116。在一个或者多个实施方式中,用于有机EL装置的材料可被用于发光层和阳极之间的至少一个层压层中。
在一个实施方式中,根据本公开的用于有机EL装置的材料用于空穴传输层108中。
基板102可以是透明的玻璃基板、使用硅形成的半导体基板或者树脂的柔性基板,等等。
阳极104可以在基板102上,并且可以使用铟锡氧化物(ITO;In2O3-SnO2)、铟锌氧化物(IZO;In2O3-ZnO)等等形成。
使用任何合适的材料,空穴注入层(HIL)106可被形成在阳极104上,厚度为大约10nm至大约150nm。材料可以包括,例如,含三苯胺的聚醚酮(TPAPEK)、4-异丙基-4’-甲基二苯基碘四(五氟苯基)硼酸盐(PPBI)、N,N’-二苯基-N,N’-双-[4-(苯基-间-甲苯基-氨基)-苯基]-苯基-4,4’-二胺(DNTPD)、酞菁化合物,比如酞菁铜、4,4’,4”-三(3-甲基苯基苯基氨基)三苯胺(间-MTDATA)、N,N’-二(1-萘基)-N,N’-二苯基联苯胺(NPB)、4,4’,4”-三(N,N-二苯基氨基)三苯胺(TDATA)、4,4’,4”-三(N,N-2-萘基苯基氨基)三苯胺(2-TNATA)、聚苯胺/十二烷基苯磺酸(PANI/DBSA)、聚(3,4-乙烯二氧噻吩)/聚(4-苯乙烯磺酸盐)(PEDOT/PSS)、聚苯胺/樟脑磺酸(PANI/CSA)、聚苯胺/聚(4-苯乙烯磺酸盐(PANI/PSS),等等。
使用根据本公开的实施方式的用于有机EL装置的材料,空穴传输层(HTL)108可被形成在空穴注入层106上,厚度为大约3nm至大约100nm。包括根据本公开的实施方式的用于有机EL装置的材料的空穴传输层108可以通过例如真空蒸发法形成。
使用任何合适的主体材料,发光层(EL)110可被形成在空穴传输层108上,厚度为大约10nm至大约60nm。在发光层110中使用的主体材料可以包括例如,三(8-羟基喹啉)铝(Alq3)、4,4’-N,N’-二咔唑-联苯(CBP)、聚(N-乙烯基咔唑)(PVK)、蒽衍生物比如,9,10-二(萘-2-基)蒽(ADN)、4,4’,4”-三(N-咔唑基)三苯胺(TCTA)、1,3,5-三(N-苯基苯并咪唑-2-基)苯(TPBI)、3-叔丁基-9,10-二(萘-2-基)蒽(TBADN)、二苯乙烯基亚芳基(DSA)和4,4’-双(9-咔唑)-2,2’-二甲基-联苯(dmCBP)。
发光层110的掺杂剂材料可以非限制性地包括苯乙烯基衍生物(比如1,4-双[2-(3-N-乙基咔唑基)乙烯基]苯(BCzVB)、4-(二-对-甲苯氨基)-4’-[(二-对-甲苯氨基)苯乙烯基]芪(DPAVB)和N-(4-((E)-2-(6-((E)-4-(二苯胺基)苯乙烯基)萘-2-基)乙烯基)苯基-N-苯基苯胺(N-BDAVBI))、苝及其衍生物(比如2,5,8,11-四-叔丁基苝(TBPe))、芘及其衍生物(比如1,1-二芘、1,4-二芘基苯和1,4-双(N,N-二苯基胺基)芘),等等。
使用例如,三(8-羟基喹啉)铝(Alq3)和/或具有含氮芳香环的材料(例如,包括吡啶环的材料比如1,3,5-三[(3-吡啶基)-苯-3-基]苯、包括三嗪环的材料比如2,4,6-三[3’-(吡啶-3-基)二苯基-3-基]1,3,5-三嗪和包括咪唑衍生物的材料比如2-(4-N-苯基苯并咪唑基-1-基苯基)-9,10-二萘基蒽),电子传输层(ETL)112可被形成在发光层110上,厚度为大约15nm至大约50nm。
使用例如,包括氟化锂(LiF)、锂-8-羟基喹啉(Liq)等的材料,电子注入层(EIL)114可被形成在电子传输层112上,厚度为大约0.3nm至大约9nm。
阴极116可以在电子注入层114上并且可以使用金属比如铝(Al)、银(Ag)、锂(Li)、镁(Mg)和钙(Ca)和/或透明材料比如ITO和IZO形成。
通过选择适当的或者合适的层形成方法,比如真空蒸发法、溅射法和/或其他合适的涂布方法(这取决于待使用的材料),可以形成各个层。
在有机EL装置100中,能够支持长的寿命的空穴传输层可以使用根据本公开的实施方式的用于有机EL装置的材料形成。
在有机EL装置100中,根据本公开的实施方式的用于有机EL装置的材料可被用作用于空穴注入层的材料。如上所述,当根据本公开的实施方式的用于有机EL装置的材料被包括在选自形成有机EL装置的多个有机层的至少一层中时,可以实现具有长的寿命的有机EL装置。
在一些实施方式中,根据本公开的用于有机EL装置的材料可被应用于使用薄膜晶体管(TFT)的有源矩阵类型(例如,有源矩阵)有机EL显示器。
实施例
制备方法
将更详细地解释根据本公开的合成用于有机EL装置的材料的方法和制造该有机EL装置的方法。然而,以下实施例仅仅是为了说明,并且本公开的范围不限于此。
化合物3的合成方法
可以根据以下方法合成化合物3。首先,合成化合物A作为中间体。
化合物A的合成
将8.00g(30.9mmol)镁金属的10mL脱水(例如,无水)THF溶液加至500mL三颈烧瓶中,随后在大约0℃搅拌。逐滴加入7.62g(30.9mmol)4-溴二苯并呋喃的脱水THF溶液,随后在室温搅拌大约2小时。逐滴加入8.00g(30.9mmol)3-溴苯甲酮的85mL脱水THF溶液,随后搅拌大约2小时并且在室温搅拌大约3小时。反应之后,将NH3Cl4的水溶液(1N)加至反应混合物,随后搅拌大约1小时。用水洗涤反应产物,并且浓缩所得有机相以产生糖果状的物质。最后,用甲醇洗涤该物质,并且干燥以产生11.6g的化合物A作为白色粉末,产率为大约88%。通过快速原子轰击质谱分析法(FAB-MS)测量的化合物A的分子量为427。
使用化合物A作为原料,根据以下方法合成化合物B。
化合物B的合成
将8.00g(18.7mmol)化合物A的60mL脱水苯溶液加至200mL三颈烧瓶,随后逐滴加入6.39mL(39.4mmol)硫酸并且在大约80℃搅拌大约2小时。反应之后,将NaHCO3的水溶液(1N)加至反应混合物,随后搅拌大约1小时。用水洗涤由此获得的产物,并且将所得有机相浓缩以获得白色固体。最后,用甲醇洗涤白色固体并且干燥以产生8.11g化合物B作为白色粉末,产率为大约89%。通过FAB-MS测量的化合物B的分子量为487。
使用化合物B作为原料,根据以下方法合成化合物C作为最终产品。
化合物3的合成
在氩气气氛下,将2.67g化合物B、1.60g双(4-联苯基)胺、0.30g的Pd2(dba)3、0.20g三-叔丁基膦和1.44g的NaOtBu加至1,000mL三颈烧瓶,随后在40mL甲苯中加热并且回流大约5小时。空气冷却之后,加入水,分离有机层,并且蒸馏溶剂。使用硅胶柱层析(使用二氯甲烷和己烷的混合物溶剂)分离由此获得的粗产物并且使用甲苯/乙醇的混合溶剂重结晶以产生2.83g化合物3为黄色固体(产率89%)。通过FAB-MS测量的化合物3的分子量为728。通过1H-NMR(CDCl3)测量的化合物3的化学位移值(δ)为7.89-7.87(m,2H)、7.71(d,1H,J=7.60Hz)、7.66(d,1H,J=7.60Hz)、7.54-7.51(m,12H)、7.41-7.21(m,10H)、7.05(d,2H,J=7.80Hz)、6.75(s,1H)、7.00-6.88(m,6H)、6.58(d,2H,J=7.80Hz)。
化合物15的合成方法
根据用于合成化合物3的基本上相同的方法合成化合物15,不同的是将用于合成化合物A的4-溴二苯并呋喃改变为4-溴二苯并噻吩。通过FAB-MS测量的化合物15的分子量为816。通过1H-NMR(CDCl3)测量的化合物15的化学位移值(δ)为7.99-7.95(m,2H)、7.71(d,1H,J=7.70Hz)、7.69(d,1H,J=7.50Hz)、7.56-7.48(m,12H)、7.38-7.21(m,7H)、7.00(d,2H,J=7.80Hz)、6.85(s,1H)、6.75-6.66(m,4H)、6.57(d,2H,J=7.80Hz)。
化合物27的合成方法
根据用于合成化合物3的基本上相同的方法合成化合物27,不同的是将用于合成化合物A的4-溴二苯并呋喃改变为2-溴二苯并呋喃。通过FAB-MS测量的化合物27的分子量为584。通过1H-NMR(CDCl3)测量的化合物27的化学位移值(δ)为7.89-7.87(m,2H)、7.71(d,1H,J=7.60Hz)、7.66(d,1H,J=7.60Hz)、7.54-7.51(m,12H)、7.41-7.21(m,7H)、7.05(d,2H,J=7.80Hz)、6.75(s,1H)、6.70-6.66(m,4H)、6.58(d,2H,J=7.80Hz)、2.22(s,3H)。
使用所得的化合物3、15和27作为空穴传输材料制造根据实施例1至3的有机EL装置。
为了比较,使用比较化合物C-1至C-3作为空穴传输材料制造根据对比例1至3的有机EL装置。
在图2中示出根据本公开的实施方式的有机EL装置200。在该实施方式中,使用透明玻璃基板形成基板202,使用ITO形成阳极204,厚度为大约150nm,使用2-TNATA形成空穴注入层206,厚度为大约60nm,形成空穴传输层208,厚度为大约30nm,使用以3%TBP掺杂的ADN形成发光层210,厚度为大约25nm,使用Alq3形成空穴传输层212,厚度为大约25nm,使用LiF形成电子注入层214,厚度为大约1nm,并且使用Al形成阴极216,厚度为大约100nm。
评估由此制造的有机EL装置200的半衰期。基于大约1,000cd/m2的最初亮度测量各个装置的半衰期。评估结果在表1中示出。在表1中,给出各个实施例和各个对比例的亮度半衰期作为相对于对比例1的亮度半衰期标准化的相对值。
表1
装置制造实施例 | 空穴传输材料 | 半衰期 |
实施例1 | 化合物3 | 1.7 |
实施例2 | 化合物15 | 1.5 |
实施例3 | 化合物27 | 1.7 |
对比例1 | 比较化合物C-1 | 1.0 |
对比例2 | 比较化合物C-2 | 0.7 |
对比例3 | 比较化合物C-3 | 0.7 |
参考表1中的结果,当与对比例1至3的有机EL装置相比时,实施例1至3的有机EL装置已经改善了(例如,增加了)寿命(长的半衰期)。在实施例1至3中,根据本公开的实施方式的用于有机EL装置的材料在芴基的9位处包括杂芳基HAr和与该杂芳基不同的取代基Ar3,芴基与胺部分结合或者连接,使得整个分子大体上是非对称的,并且材料可以是更加无定形的。因此,电荷传输可以变得顺畅(例如,可被改善),并且有机EL装置的寿命可被改善。在对比例1至3中,通过未共享的电子对(例如,孤电子对)可以二苯并呋喃环和/或氮上产生位阻斥力,并且有机EL装置的寿命缩短(例如,减少)。
由表1中的结果可知,当与使用根据对比例的比较化合物的有机EL装置相比时,使用根据本公开的实施方式的用于有机EL装置的材料的有机EL装置具有更长的寿命。根据本公开的实施方式的用于有机EL装置的材料在芴基的9位处包括杂芳基HAr和与该杂芳基不同的取代基Ar3,芴基与胺部分结合或者连接,并且包括该材料的有机EL装置的寿命可被增加或者改善。
根据本公开的用于有机EL装置的材料具有宽的能隙,并且该材料应用于红色和/或绿色发光区中的OLED可以是可能的。
根据本公开的一个或多个实施方式,提供了用于具有长的寿命的有机EL装置的材料以及使用该材料的有机EL装置。用于有机EL装置的材料在芴基的9位处包括杂芳基HAr和与该杂芳基不同的取代基,芴基与胺结合或者连接。因此,电荷传输可以变得顺畅(例如,可被改善),并且有机EL装置的寿命可被改善。以上描述的效果在蓝色发光区中可以是显著的。
尽管已经参考附图描述了一个或者多个实例实施方式,但是本领域普通技术人员理解的是,在不背离如权利要求及其等价物所限定的本公开的精神和范围的情况下可以在其中进行形式和细节的各种改变。
如本文所使用的,当在一列要素之后时,表述比如“……中的至少一个”、“……中的一个”、“选自……中的至少一个”和“选自……中的一个”修饰整列要素,并且不修饰该列中的单个要素。进一步,当描述本公开的实施方式时,使用“可以”指的是“本公开的一个或多个实施方式”。
此外,如本文所使用的,术语“使用”、“正在使用”和“所使用的”可被认为分别与术语“利用”、“正在利用”和“所利用的”同义。
如本文所使用的,术语“基本上”、“大约”以及类似术语用作近似的术语,而不是程度的术语,并且意欲为说明可被本领域普通技术人员所认识到的测量值或计算值的固有偏差。
同样地,本文所描述的任何数值范围意欲包括归入所描述的范围内的相同数值精度的全部子范围。例如,范围“1.0至10.0”意欲包括所描述的最小值1.0和所描述的最大值10.0之间(并且包括所描述的最小值1.0和所描述的最大值10.0)的所有子范围,即,具有等于或者大于1.0的最小值和等于或者小于10.0的最大值,诸如,例如,2.4至7.6。本文描述的任何最大数值限制意欲包括归入其中的所有较低数值限制,并且本说明书中描述的任何最小数值限制意欲包括归入其中的所有较高数值限制。因此,申请人保留修改包括权利要求的本说明书以明确描述归入本文所明确描述的范围之内任意子范围的权利。
以上所公开的主题被认为是例证性的而非限制性的,并且所附权利要求及其等价物意欲涵盖所有这样的更改、增强和落入本公开的真实精神和范围内的其他实施方式。因此,就法律允许的最大程度而言,本公开的范围由权利要求及其等价物的最广泛的可允许的解释确定,并且不应限制或者限于以上详细描述。
Claims (10)
1.一种由式1表示的用于有机电致发光装置的材料:
式1
其中在式1中,
Ar1和Ar2各自独立地选自具有6至30个用于形成环的碳原子的取代的或者未取代的芳基和具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基,
Ar3选自具有6至30个用于形成环的碳原子的取代的或者未取代的芳基、具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基和具有1至6个碳原子的烷基,
HAr是具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基,
L选自直接连接、具有6至30个用于形成环的碳原子的取代的或者未取代的亚芳基和具有5至30个用于形成环的碳原子的取代的或者未取代的亚杂芳基,并且
HAr和Ar3彼此不同。
2.权利要求1所述的材料,其中Ar1至Ar3各自独立地为具有6至30个用于形成环的碳原子的取代的或者未取代的芳基。
3.权利要求1所述的材料,其中HAr选自取代的或者未取代的二苯并呋喃基和取代的或者未取代的二苯并噻吩基。
4.权利要求1所述的材料,其中所述由式1表示的用于有机电致发光装置的材料为选自以下化合物1至132和135至138中的至少一个:
5.一种有机电致发光装置,其在至少一层中包括由式1表示的用于有机电致发光装置的材料:
式1
其中在式1中
Ar1和Ar2各自独立地选自具有6至30个用于形成环的碳原子的取代的或者未取代的芳基和具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基,
Ar3选自具有6至30个用于形成环的碳原子的取代的或者未取代的芳基、具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基和具有1至6个碳原子的烷基,
HAr是具有5至30个用于形成环的碳原子的取代的或者未取代的杂芳基,
L选自直接连接、具有6至30个用于形成环的碳原子的取代的或者未取代的亚芳基和具有5至30个用于形成环的碳原子的取代的或者未取代的亚杂芳基,并且
HAr和Ar3彼此不同。
6.权利要求5所述的有机电致发光装置,其中所述用于有机电致发光装置的材料被包括在发光层和阳极之间的至少一个层压层中。
7.权利要求5所述的有机电致发光装置,其中所述用于有机电致发光装置的材料被包括在空穴传输层中。
8.权利要求5所述的有机电致发光装置,其中Ar1至Ar3各自独立地为具有6至30个用于形成环的碳原子的取代的或者未取代的芳基。
9.权利要求5所述的有机电致发光装置,其中HAr选自取代的或者未取代的二苯并呋喃基和取代的或者未取代的二苯并噻吩基。
10.权利要求5所述的有机电致发光装置,其中所述由式1表示的用于有机EL装置的材料为选自以下化合物1至132和135至138中的至少一个:
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KR20210090782A (ko) * | 2020-01-10 | 2021-07-21 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
JP2023531480A (ja) * | 2020-06-26 | 2023-07-24 | エルティー・マテリアルズ・カンパニー・リミテッド | ヘテロ環化合物およびそれを用いた有機発光素子 |
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EP3750875A2 (en) | 2019-06-14 | 2020-12-16 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Nitrogen-containing compound, organic electroluminescent device and photoelectric conversion device |
CN111875580A (zh) * | 2020-08-18 | 2020-11-03 | 长春海谱润斯科技有限公司 | 一种二苯并噻吩衍生物及其有机发光器件 |
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Also Published As
Publication number | Publication date |
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JP2016192464A (ja) | 2016-11-10 |
US20160293843A1 (en) | 2016-10-06 |
KR20160118123A (ko) | 2016-10-11 |
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