CN114805386A - 有机化合物、主体材料和有机光电器件 - Google Patents
有机化合物、主体材料和有机光电器件 Download PDFInfo
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- CN114805386A CN114805386A CN202210640183.8A CN202210640183A CN114805386A CN 114805386 A CN114805386 A CN 114805386A CN 202210640183 A CN202210640183 A CN 202210640183A CN 114805386 A CN114805386 A CN 114805386A
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MHJUNMARMFAUBI-UHFFFAOYSA-N n-phenyliminobenzamide Chemical compound C=1C=CC=CC=1C(=O)N=NC1=CC=CC=C1 MHJUNMARMFAUBI-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C07D491/14—Ortho-condensed systems
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Abstract
本发明公开了有机化合物、主体材料和有机光电器件,其化学结构如式(Ⅰ)所示,其中A和B独立选自氢、氘、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、取代或未取代的C3~C30环烷基、或者取代或未取代的C3~C30杂环烷基;Z1‑Z8各自独立选自CR2或N;X1‑X4各自独立选自CR3R4、NR5、O或S等,本发明还提供一种主体材料,包含至少一种第一主体化合物(通式(Ⅱ)表示)和至少一种第二主体化合物(通式(Ⅲ)表示)。本发明的有机化合物通过引入并环类基团使化合物具有较大的三线态能级和良好的热稳定性,用于有机光电器件能提高器件的发光效率和使用寿命。
Description
技术领域
本发明属于有机光电材料领域,具体涉及有机化合物、主体材料和有机光电器件。
背景技术
有机电致发光器件(Organic Light Emission Diodes,OLED)是一类具有类三明治结构的器件,包括正负电极膜层及夹在电极膜层之间的有机功能材料层。目前,该技术已被广泛应用于新型照明灯具、智能手机及平板电脑等产品的显示面板,进一步还将向电视等大尺寸显示产品应用领域扩展,是一种发展快、技术要求高的新型显示技术。OLED材料在信息显示材料、有机光电子材料等领域中的应用具有极大的研究价值和应用前景。随着多媒体信息技术的发展,对平板显示器件性能的要求越来越高,目前主要的显示技术有等离子显示器件、场发射显示器件和有机电致发光显示器件(OLED)。其中,OLED具有自身发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列优点,与液晶显示器件相比,OLED不需要背光源,视角更宽,功耗低,其响应速度是液晶显示器件的1000倍,具有更广阔的应用前景。
自OLED第一次被报道以来,许多学者致力于研究如何提高器件效率和稳定性。Forrest和Thompson研究团队发现过渡金属配合物能应用于Ph OLEDs(phosphorescentOLEDs),磷光材料存在很强的自旋轨道耦合作用,能同时利用单线态和三线态激子,使磷光电致发光器件内量子效率在理论上达到了100%。然而,磷光材料激发态寿命较长,当三线态激子浓度较高时容易形成三线态-三线态凐灭和三线态-极化子间凐灭,常常将磷光材料作为客体参入到主体材料中,以此来降低自浓度淬灭过程。因此,在磷光有机电致发光器件中选择合适的主体材料也是非常重要,其中主体材料必备特性:(1)拥有较高的三线态能级;(2)具有较好的载流子迁移率且能与相邻层能级匹配;(3)具有高的热稳定性和成膜稳定性。目前,随着OLED显示和照明广泛的商业化应用,客户终端对OLED屏体光电及寿命要求的不断提升,为了应对这类需求,除在OLED面板制程工艺上不断完善外,开发出能够满足更高器件指标的OLED材料尤为重要,特别是开发稳定高效的主体材料实现降低驱动电压、提高器件发光效率和延长器件寿命的目的,具有重要的实际应用价值。
发明内容
本发明的目的在于提供一类稳定高效的可用于红色和绿色磷光有机电致发光器件的新型有机材料,该材料具有较高的三线态能级、具有较好的载流子迁移率且能与相邻能级匹配,具有较高的热稳定性和成膜稳定性,应用于红色和绿色磷光OLED器件中能够降低驱动电压,提高器件发光效率。
为实现上述目的,本发明一方面提供一种有机化合物,其化学结构如式(Ⅰ)所示:
在式(Ⅰ)中,A和B独立选自氢、氘、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、取代或未取代的C3~C30环烷基、或者取代或未取代的C3~C30杂环烷基;
Z1-Z8各自独立选自CR2或N;
X1-X4各自独立选自CR3R4、NR5、O或S;
R1-R5相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基、取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C6~C30杂芳基、或者与相邻的原子键合成环;
Ar1选自取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环。
本发明另一方面还提供一种主体材料,该主体材料包含至少一种第一主体化合物和至少一种第二主体化合物,其中第一主体化合物由通式(Ⅱ)表示,且第二主体化合物由通式(Ⅲ)表示:
式(Ⅱ)和(Ⅲ)中,C和D独立选自氢、氘、取代或未取代的C6~C30芳基、或取代或未取代的C5~C30杂芳基、取代或未取代的C3~C30环烷基、或者取代或未取代的C3~C30杂环烷基;
Z9-Z16各自独立选自CR7或N;
X5-X8各自独立选自单键、CR8R9、NR10、O或S;
R6-R10相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基、取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环;
Ar2、Ar3、Ar4和Ar5各自独立选自取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环。
本发明另一方面还提供一种有机光电器件,其包括第一电极、第二电极和有机层,其中所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层,且所述有机层包含所述有机化合物或所述主体材料中的一种或多种,特别是其中发光层包含所述有机化合物或所述主体材料中的一种或多种;所述有机光电器件包括有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
本发明另一方面还提供一种显示或照明装置,其包括所述的有机光电器件。
与现有技术相比,本发明的有益效果为:本发明提供的有机化合物由于并环类基团的引入,使化合物具有较大的三线态能级,且具有良好的热稳定性。同时,本发明的有机化合物应用到有机光电器件上,能使器件具有较高的发光效率和稳定性,有效提升器件的发光效率和使用寿命。
具体实施方式
以下详细说明具体公开的化合物及其在有机光电器件中的应用的实施方式,本领域技术人员可由本说明书所揭露的内容轻易地了解本发明的其他优点与功效,还可以通过另外不同的具体实施方式加以实施或应用,本说明书中的各项细节也可以基于不同观点与应用,在没有背离本发明的精神下进行各种修饰或改变。
在进一步描述本发明具体实施方式之前,应理解本发明的保护范围不局限于下述特定的具体实施方案,本发明实施例中使用的术语是为了描述特定的具体实施方案,而不是为了限制本发明的保护范围,在本发明说明书和权利要求书中,除非文中另外明确指出,单数形式“一个”、“一”和“这个”包括复数形式。
当实施例给出数值范围时,应理解,除非本发明另有说明,每个数值范围的两个端点以及两个端点之间任何一个数值均可选用。除非另外定义,本发明中使用的所有技术和科学术语与本技术领域技术人员通常理解的意义相同。除实施例中使用的具体方法、设备、材料外,根据本技术领域的技术人员对现有技术的掌握及本发明的记载,还可以使用与本发明实施例中所述的方法、设备、材料相似或等同的现有技术的任何方法、设备和材料来实现本发明。
本发明的发明人经过大量探索和研究提供一种基于咔唑衍生物的有机化合物,本发明的有机化合物应用到有机光电器件上,能使器件具有较高的器件效率,同时化合物分子具有高的稳定性,能进一步提升器件的发光效率和使用寿命。
本发明中的取代基的实例描述如下,但取代基并不限于此:
【取代或未取代】是指经选自以下的一个或更多个取代基取代:氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基团、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基膦基和杂芳基,苊基,化合物基团,或未取代;或者经连接以上示例的取代基中的两个或更多个取代基的取代基取代,或未取代。例如,“连接两个或更多个取代基的取代基”可包括联苯基,即联苯基可为芳基,或者为连接两个苯基的取代基。
【烷基】可为直链或支链的,并且碳原子数没有特别限制。在一些实施例中,烷基包括但不限于甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、4-甲基己基、5-甲基己基。
以上对烷基的描述也可用于芳烷基、芳烷基胺基、烷基芳基和烷基胺基中的烷基。
【杂烷基】可为含杂原子的直链或支链的烷基,并且碳原子数没有特别限制。在一些实施例中,杂烷基包括但不限于可以烷氧基、烷硫基、烷基磺酰基等。烷氧基例如可以包括但不限于甲氧基、乙氧基、正丙氧基、异丙氧基(isopropoxy)、异丙氧基(i-propyloxy)、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基、苄氧基、对甲基苄氧基等。烷硫基例如可以包括但不限于甲硫基、乙硫基、正丙硫基、异丙硫基、异丙硫基、正丁硫基、异丁硫基、叔丁硫基、仲丁硫基、正戊硫基、新戊硫基、异戊硫基、正己硫基、3,3-二甲基丁硫基、2-乙基丁硫基、正辛硫基、正壬硫基、正癸硫基、苄硫基等。
【环烷基】可为环状的,并且碳原子数没有特别限制。在一些实施例中,环烷基包括但不限于环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等。
【芳基】没有特别限定,芳基可为单环芳基或多环芳基。在一些实施例中,单环芳基包括但不限于苯基、联苯基、三联苯基、四联苯基、五联苯基等。多环芳基包括但不限于萘基、蒽基、菲基、芘基、苝基、芴基等。芴基可为经取代的,例如9,9’-二甲基芴基、9,9’-二苯并芴基等。此外,取代基中的两个可彼此结合形成螺环结构,例如9,9’-螺二芴基等。
以上对芳基的描述可用于亚芳基,不同之处在于亚芳基为二价。
以上对芳基的描述可用于芳氧基、芳基硫基、芳基磺酰基、芳基膦基、芳烷基、芳烷基胺基、芳烯基、烷基芳基、芳基胺基和芳基杂芳基胺基中的芳基。
【杂芳基】包含N、O、P、S、Si和Se中的一个或多个作为杂原子,杂芳基包括但不限于吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、咪唑基、吡唑基、唑基、异唑基、噻唑基、异噻唑基、三唑基、二唑基、噻二唑基、二噻唑基、四唑基、吡喃基、噻喃基、吡嗪基、嗪基、噻嗪基、二氧杂环己烯基、三嗪基、四嗪基、喹啉基、异喹啉基、喹啉基、喹唑啉基、喹喔啉基、萘啶基、吖啶基、呫吨基、菲啶基、二氮杂萘基、三氮杂茚基、吲哚基、二氢吲哚基、中氮茚基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、苯并噻唑基、苯并噁唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、茚并咔唑基、吩嗪基、咪唑并吡啶基、吩嗪基、菲啶基、菲咯啉基、吩噻嗪基、咪唑并吡啶基、咪唑并菲啶基、苯并咪唑并喹唑啉基、苯并咪唑并菲啶基、螺[芴-9,9'-氧杂蒽]、苯联萘基、二萘并呋喃基、萘苯并呋喃基、二萘并噻吩基、萘苯并噻吩基、三苯基氧化膦、三苯基硼烷等。
以上对杂芳基的描述可用于杂芳基胺基和芳基杂芳基胺基中的杂芳基。
以上对杂芳基的描述可用于亚杂芳基,不同之处在于亚杂芳基为二价的。
本发明一方面提供一种有机化合物,其化学结构如式(Ⅰ)所示:
在式(Ⅰ)中,A和B独立选自氢、氘、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、取代或未取代的C3~C30环烷基、或者取代或未取代的C3~C30杂环烷基;
Z1-Z8各自独立选自CR2或N;
X1-X4各自独立选自CR3R4、NR5、O或S;
R1-R5相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基、取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环;
Ar1选自取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环。
作为优选,在式(Ⅰ)中,Ar1选自如下基团中的一个或多个:
其中,R11-R17相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基、取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环。
具体地,上述化学结构可为未取代或者选自以下的一个或多个取代基取代。例如可以是氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、胺基、氧化膦基团、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基杂芳基胺基、芳基膦基和杂芳基等。
作为优选,式(Ⅰ)所示的有机化合物选自以下化学结构中的一种或多种:
上述有机化合物以多杂环结构为母体,该母体结构具有良好的热稳定性,同时具有合适的HOMO、LUMO能级和Eg,具有较高的三线态能级、较好的载流子迁移率且能与相邻能级匹配,具有较高的热稳定性和成膜稳定性,可以作为新型OLED材料应用于OLED器件中,作为主体材料使用可以有效地提升器件的效率和寿命。
本发明另一方面还提供一种主体材料,该主体材料包含至少一种第一主体化合物和至少一种第二主体化合物,其中第一主体化合物由通式(Ⅱ)表示,且第二主体化合物由通式(Ⅲ)表示:
式(II)和(III)中,C和D独立选自氢、氘、取代或未取代的C6~C30芳基、或取代或未取代的C5~C30杂芳基、取代或未取代的C3~C30环烷基、或者取代或未取代的C3~C30杂环烷基;
Z9-Z16各自独立选自CR7或N;
X5-X8各自独立选自单键、CR8R9、NR10、O或S;
R6-R10相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基、取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C6~C30杂芳基、或者与相邻的原子键合成环;
Ar2、Ar3、Ar4和Ar5各自独立选自取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环。
作为优选,式(II)和(III)中,Ar2、Ar3、Ar4和Ar5各自独立选自选自如下基团中的一个或多个:
其中,X5和X6相同或不相同,独立选自单键、CR20R21、SiR22R23、NR24、O或S;
M17和M18相同或不相同,各自独立选自CR25R26、SiR27R28、NR29、O或S;
Z17~Z54相同或不相同,各自独立选自CR30R31、SiR32R33、NR34、O或S;
R18~R34相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基;取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C6~C30杂芳基、或者与相邻的原子键合成环;
E选自氢、氘、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、或取代或未取代的C5~C30杂芳基。
作为优选,式(II)所示的第一主体化合物选自以下化学结构中的一种或多种:
作为优选,式(III)所示的第二主体化合物选自以下化学结构中的一种或多种:
本发明另一方面还提供一种有机层,包括本发明前述的有机化合物或主体材料。
本发明另一方面还提供如本发明前述的有机化合物、主体材料和/或有机层在有机光电器件中的应用。
本发明另一方面还提供一种有机光电器件,其包括第一电极、第二电极和有机层,其中有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层,且有机层包含上述有机化合物中的一种或多种、或上述主体材料中的一种或多种。作为优选,发光层包含上述有机化合物中的一种或多种、或上述主体材料中的一种或多种。
作为优选,本发明的有机光电器件可以为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
本发明提供的有机光电器件中,包括第一电极、第二电极、以及设置在第一电极和第二电极之间的一个或多个有机层,为底部或顶部发光器件结构,其有机层可为单层结构,也可为层合有两个或多个有机层的多层串联结构,有机层如具有包括空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层,可使用制备有机光电器件的常见方法和材料来制备,采用本发明的上述有机化合物或主体材料作为有机光电器件的有机层。
本发明提供的有机光电器件中,第一电极作为阳极层,阳极材料例如可以是具有大功函数的材料,使得空穴顺利地注入有机层。例如也可以是金属、金属氧化物、金属和氧化物的组合、导电聚合物等,金属氧化物例如可以是氧化铟锡(ITO)、氧化锌、氧化铟、和氧化铟锌(IZO)等。
本发明提供的有机光电器件中,第二电极作为阴极层,阴极材料例如可以是具有小功函数的材料,使得电子顺利地注入有机层,例如也可以是金属或多层结构材料,金属例如可以是镁、银、钙、钠、钾、钛、铟、钇、锂、钆、铝、锡和铅、或其合金,阴极材料优选镁和/或银。
本发明提供的有机光电器件中,空穴注入层的材料优选最高占据分子轨道(HOMO)介于阳极材料的功函数与周围有机层的HOMO之间的材料,作为在低电压下有利地从阳极接收空穴的材料。
本发明提供的有机光电器件中,空穴传输层的材料优选对空穴具有高迁移率的材料,适合作为接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,包括但不限于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等。
本发明提供的有机光电器件中,本发明提供的有机化合物可以应用于器件的发光层。
本发明提供的有机光电器件中,电子传输层的材料是对电子具有高迁移率的材料,适合作为有利地接收来自阴极的电子并将电子传输至发光层的材料。
本发明提供的有机光电器件中,覆盖层的材料通常具有高折射率,可有助于有机发光器件的光效率提高,尤其是有助于外部发光效率提高。
本发明提供的有机光电器件中,有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管等。
本发明另一方面还提供一种显示或照明装置,其包括上述有机光电器件。
以下通过特定的具体实例说明本发明的实施方式。
合成实施例:
上述式(I)所示的有机化合物的合成可以使用已知的方法进行,例如使用镍、钯等过渡金属的交叉偶合反应也可以使用镁或锌等过渡金属的C-C、C-N偶联生成反应。上述反应限于反应条件温和、各种官能团的选择性优越等特点,优选Suzuki,Buchwald反应。本发明的有机化合物用以下实施例举例说明,但并不限于这些实施例举例的有机化合物和合成方法。本发明的初始原料和溶剂和一些常用的OLED中间体类等产品购于国内的OLED中间体厂商;各种钯催化剂,配体等购于sigma-Aldrich公司。1H-NMR数据使用JEOL(400MHz)核磁共振仪来测定,HPLC数据使用岛津LC-20AD高效液相仪来测定。
以下合成实施例中使用的物质为:
实施例1
化合物1的合成
1)中间体1-1的合成
在氩气氛围下,向反应容器中加入化合物1-A 37.6克(100mmol),化合物1-B 26.2克(100mmol),碳酸铯39.1克(120mmol),乙酸钯225毫克(1mmol),4,5-双二苯基膦-9,9-二甲基氧杂蒽1.7克(3mmol)和1000mL甲苯(toluene),在110℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到35.7克化合物1-1,HPLC纯度99.6%,收率70%。LC MS:M/Z 509.04(M+)。
2)中间体1-2的合成
在氩气氛围下,向反应容器中加入化合物1-1 51.0克(100mmol),碳酸钾27.6克(300mmol),乙酸钯450毫克(2mmol),三环己基膦四氟硼酸盐1.5克(4mmol)和1000mL甲苯(toluene),在110℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到35.7克化合物1-2,HPLC纯度99.7%,收率83%。LC MS:M/Z 429.12(M+)。
3)化合物1的合成
在氩气氛围下,向反应容器中加入化合物1-2 43.0克(100mmol),化合物1-C 28.5克(100mmol),叔丁醇钠23.4克(240mmol),双二亚苄基丙酮钯575毫克(1mmol%),三叔丁基膦四氟硼酸盐580毫克(2mmol%)和1000mL二甲苯(xylene),在140℃加热搅拌15小时。反应混合物冷却到室温,加入1000ml水,过滤,滤饼用大量水洗涤,真空干燥,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到54.5克化合物1,HPLC纯度99.9%,收率86%。LCMS:M/Z 633.19(M+)。
实施例2
化合物22的合成
除了起始原料更换为22-A、22-B和22-C以外,其他与实施例1相同。LC MS:M/Z729.15(M+)。HPLC纯度:99.9%,总收率:49%;
实施例3
化合物54的合成
除了起始原料更换为54-A、54-B和54-C以外,其他与实施例1相同。LC MS:M/Z633.19(M+)。合成总收率:46%;HPLC纯度:99.9%。
实施例4
化合物89的合成
除了起始原料更换为89-A、89-B和89-C以外,其他与实施例1相同。LC MS:M/Z700.25(M+)。合成总收率:51%;HPLC纯度:99.9%。
实施例5
化合物117的合成
除了起始原料更换为117-A、117-B和54-C以外,其他与实施例1相同。LC MS:M/Z651.18(M+)。合成总收率:50%;HPLC纯度:99.9%。
实施例6
化合物134的合成
除了起始原料更换为134-A、134-B、和54-C以外,其他与实施例1相同。LC MS:M/Z712.28(M+)。合成总收率:48%;HPLC纯度:99.9%。
实施例7
化合物146的合成
除了起始原料更换为146-A、146-B和54-C以外,其他与实施例1相同。LC MS:M/Z661.20(M+)。合成总收率:49%;HPLC纯度:99.9%。
实施例8
化合物172的合成
除了起始原料更换为172-A、172-B和89-C以外,其他与实施例1相同。LC MS:M/Z662.19(M+)。合成总收率:49%;HPLC纯度:99.9%。
实施例9
化合物188的合成
除了起始原料更换为188-A、146-B和54-C以外,其他与实施例1相同。LC MS:M/Z675.23(M+)。合成总收率:56%;HPLC纯度:99.9%。
实施例10
化合物211的合成
除了起始原料更换为89-A、211-B和54-C以外,其他与实施例1相同。LC MS:M/Z785.25(M+)。合成总收率:59%;HPLC纯度:99.9%。
实施例11
化合物H-2的合成
除了起始原料更换为H-2-A、H-2-B和H-2-C以外,其他与实施例1相同。LC MS:M/Z539.63(M+)。合成总收率:52%;HPLC纯度:99.9%。
实施例12
化合物H-23的合成
除了起始原料更换为H-23-A、H-23-B和H-23-C以外,其他与实施例1相同。LC MS:M/Z 660.19(M+)。合成总收率:52%;HPLC纯度:99.9%。
实施例13
化合物H-56的合成
除了起始原料更换为H-56-A、H-56-B和H-56-C以外,其他与实施例1相同。LC MS:M/Z 681.27(M+)。合成总收率:55%;HPLC纯度:99.9%。
实施例14
化合物H-93的合成
除了起始原料更换为H-93-A、H-93-B和H-93-C以外,其他与实施例1相同。LC MS:M/Z 781.97(M+)。合成总收率:54%;HPLC纯度:99.9%。
实施例15
化合物H-118的合成
除了起始原料更换为H-118-A、H-118-B和H-118-C以外,其他与实施例1相同。LCMS:M/Z 631.20(M+)。合成总收率:58%;HPLC纯度:99.9%。
实施例16
化合物H-136的合成
除了起始原料更换为H-136-A、H-136-B和H-136-C以外,其他与实施例1相同。LCMS:M/Z 697.24(M+)。合成总收率:53%;HPLC纯度:99.9%。
实施例17
化合物H-148的合成
除了起始原料更换为H-148-A、H-148-B和H-148-C以外,其他与实施例1相同。LCMS:M/Z 697.24(M+)。合成总收率:53%;HPLC纯度:99.9%。
实施例18
化合物H-175的合成
除了起始原料更换为H-175-A、H-175-B和H-175-C以外,其他与实施例1相同。LCMS:M/Z 673.13(M+)。合成总收率:52%;HPLC纯度:99.9%。
实施例19
化合物H-190的合成
除了起始原料更换为H-190-A、H-190-B和H-190-C以外,其他与实施例1相同。LCMS:M/Z 679.11(M+)。合成总收率:55%;HPLC纯度:99.9%。
实施例20
化合物H-211的合成
除了起始原料更换为H-211-A、H-211-B和H-211-C以外,其他与实施例1相同。LCMS:M/Z 783.26(M+)。合成总收率:55%;HPLC纯度:99.9%。
实施例21
化合物E-4的合成
1)中间体E-4-1的合成
氩气氛围下,反应器中加入E-4-A 31.5g(100mmol)、E-4-B 21.2g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到28.2g的化合物E-4-1,收率70%,HPLC纯度99.1%。
2)化合物E-4的合成
氩气氛围下,反应器中加入E-4-1 40.2g(100mmol)、E-4-C 33.9g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到46.3g的化合物E-4,收率75%,HPLC纯度99.9%。LC MS:M/Z 616.19(M+)
实施例22
化合物E-8的合成
除了起始原料更换为E-8-C以外,其他与实施例21相同。LC MS:M/Z 666.21(M+)。合成总收率:45%;HPLC纯度:99.9%。
实施例23
化合物E-29的合成
除了起始原料更换为E-29-B和E-29-C以外,其他与实施例21相同。LC MS:M/Z525.18(M+)。合成总收率:45%;HPLC纯度:99.9%。
实施例24
化合物E-36的合成
除了起始原料更换为E-36-B和E-36-C以外,其他与实施例21相同。LC MS:M/Z577.25(M+)。合成总收率:42%;HPLC纯度:99.9%。
实施例25
化合物E-48的合成
除了起始原料更换为E-48-C以外,其他与实施例21相同。LC MS:M/Z 601.22(M+)。合成总收率:40%;HPLC纯度:99.9%。
实施例26
化合物E-53的合成
除了起始原料更换为E-53-B和E-53-C以外,其他与实施例21相同。LC MS:M/Z653.26(M+)。合成总收率:42%;HPLC纯度:99.9%。
实施例27
化合物E-65的合成
除了起始原料更换为E-65-A、E-65-B和E-53-C以外,其他与实施例21相同。LC MS:M/Z 601.11(M+)。合成总收率:43%;HPLC纯度:99.9%。
实施例28
化合物E-78的合成
除了起始原料更换为E-65-A、E-78-B和E-29-B以外,其他与实施例21相同。LC MS:M/Z 689.21(M+)。合成总收率:46%;HPLC纯度:99.9%。
实施例29
化合物E-88的合成
除了起始原料更换为E-88-A、E-29-B和E-88-C以外,其他与实施例21相同。LC MS:M/Z 599.20(M+)。合成总收率:43%;HPLC纯度:99.9%。
实施例30
化合物E-95的合成
除了起始原料更换为E-95-A、E-95-B和E-95-C以外,其他与实施例21相同。LC MS:M/Z 690.25(M+)。合成总收率:46%;HPLC纯度:99.9%。
器件实施例1:单主体材料有机电致发光器件的制备
本发明有机光电器件的基本结构模型为:ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/EML(本发明的有机化合物):RD(Ir配合物)=94:6(40nm)/ETL(30nm)/LiF(1nm)/Al(80nm)。
本发明有机光电器件的制造方法:
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟。
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后,控制体系压力在10-6托,接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN,40nm的TAPC和10nm的TCTA。
(3)在上述TCTA上蒸镀厚度为40nm的发光层(EML),其中本发明化合物1与RD的质量比为94:6。
(4)在上述发光层上蒸镀厚度为30nm的电子传输层(ETL)材料。
(5)在上述电子传输层上蒸镀厚度为1nm的LiF作为电子注入层。
(6)最后在上述电子注入层上蒸镀厚度为80nm的Al作为阴极,且利用玻璃封装盖对器件进行封装。
器件实施例2-10
除了在形成发光层时,分别以化合物22、54、89、117、134、146、172、188、和211替代化合物1外,采用与器件实施例1相同的方法制作有机电致发光器件。
器件对比例1-2
除了在形成发光层时,分别以化合物RH-01、化合物RH-02替代化合物1外,采用与器件实施例1相同的方法制作有机电致发光器件。
对以上制得的有机电致发光器件,通过计算机控制的Keithley 2400测试系统计算得到工作电压和效率。使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量系统得到黑暗条件下的器件寿命。每一组器件实施例和器件对比例1均与器件对比例2的器件在同一批次中产出并测试,如表1所示。
表1
根据表1的结果可知,作发光器件的发光层时,器件实施例1–10所使用的化合物与器件对比例1–2中使用的化合物形成的器件相比,发光效率均有所提高(最高达到20%),寿命提高高达40%以上。
据此,上述实施例和对比例中的器件结构除了发光层不同外,其它均一致,基于RH-01和RH-02的器件性能为参考,包含本发明的化合物的器件的电流效率有了显著提升,同时其寿命也有所提升。
器件实施例11:多主体材料有机电致发光器件的制备
器件的基本结构模型为:ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/EML(本发明的主体材料:RD(Ir配合物)(40nm)=98:2/ETL(30nm)/LiF(1nm)/Al(80nm)
本发明有机光电器件的制造方法:
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟;
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后,控制体系压力在10-6托,接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN、40nm的TAPC和10nm的TCTA;
(3)蒸镀厚度为40nm的发光层(EML)(其中,本发明的主体材料与RD的质量比为98:2),其中在该主体材料中,第一主体化合物H-2与所述第二主体化合物E-4的质量比为2:3;
(4)蒸镀厚度为30nm的电子传输层(ETL)材料;
(5)蒸镀厚度为1nm的LiF作为电子注入层;
(6)最后蒸镀厚度为80nm的Al作为阴极,且利用玻璃封装盖对器件进行封装,器件测试结果见表2。
器件实施例12-20
除了在形成发光层时,分别以化合物组合物H-23和E-8、H-56和E-29、H-93和E-36、H-118和E-48、H-136和E-53、H-148和E-65、H-175和E-78、H-190和E-88、H-211和E-95替代化合物H-2和E-4外,采用与器件实施例11相同的方法制作有机电致发光器件。
器件对比例3~4
除了在形成发光层时,分别以化合物CBP、化合物Ref1和Ref2替代化合物2和4以外,采用与器件实施例11相同的方法制作有机电致发光器件。
对以上制得的有机电致发光器件,通过计算机控制的Keithley 2400测试系统计算得到工作电压和效率,使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量系统得到黑暗条件下的器件寿命,每一组器件实施例和器件对比例3和4的器件在同一批次中产出并测试,如表2所示。
表2
根据表2的结果可知,作发光器件的发光层时,器件实施例11–20所使用的化合物与器件对比例1–2中使用的化合物形成的器件相比,电压均有所降低,发光效率均有所提高(最高达到20%),寿命提高高达40%以上。
据此,上述实施例和对比例中的器件结构除了发光层不同外,其它均一致,基于Ref1和Ref2的器件性能为参考,包含本发明的有机化合物的器件的电流效率有了显著提升,同时其寿命也有所提升。
Claims (12)
1.一种有机化合物,其化学结构如式(Ⅰ)所示:
在式(Ⅰ)中,A和B独立选自氢、氘、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、取代或未取代的C3~C30环烷基、或者取代或未取代的C3~C30杂环烷基;
Z1-Z8各自独立选自CR2或N;
X1-X4各自独立选自CR3R4、NR5、O或S;
R1-R5相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基、取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环;
Ar1选自取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环。
4.一种主体材料,其特征在于,所述主体材料包含至少一种第一主体化合物和至少一种第二主体化合物,其中所述第一主体化合物由通式(Ⅱ)表示,且所述第二主体化合物由通式(Ⅲ)表示:
式(Ⅱ)和(Ⅲ)中,C和D独立选自氢、氘、取代或未取代的C6~C30芳基、或取代或未取代的C5~C30杂芳基、取代或未取代的C3~C30环烷基、或者取代或未取代的C3~C30杂环烷基;
Z9-Z16各自独立选自CR7或N;
X5-X8各自独立选自单键、CR8R9、NR10、O或S;
R6-R10相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基、取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环;
Ar2、Ar3、Ar4和Ar5各自独立选自取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环。
5.根据权利要求4所述的主体材料,其特征在于,Ar2、Ar3、Ar4和Ar5各自独立选自选自如下基团中的一个或多个:
其中,X5和X6相同或不相同,独立选自单键、CR20R21、SiR22R23、NR24、O或S;
M17和M18相同或不相同,各自独立选自CR25R26、SiR27R28、NR29、O或S;
Z17~Z54相同或不相同,各自独立选自CR30R31、SiR32R33、NR34、O或S;
R18~R34相同或不相同,各自独立选自氢、氘、取代或未取代的直链或支链的C1~C30烷基;取代或未取代的C1~C30杂烷基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、取代或未取代的C5~C30杂芳基、或者与相邻的原子键合成环;
E选自氢、氘、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基、取代或未取代的C6~C30芳基、或取代或未取代的C5~C30杂芳基。
8.权利要求1~3中任一项所述有机化合物或权利要求4~7任一项所述主体材料在有机光电器件中的应用。
9.一种有机光电器件,其特征在于,其包括第一电极、第二电极和有机层,其中所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层,且所述有机层包含权利要求1~3中任一项所述有机化合物中的一种或多种、或权利要求4~7任一项所述主体材料中的一种或多种。
10.根据权利要求9所述的有机光电器件,其特征在于,所述发光层包含权利要求1~3中任一项所述有机化合物中的一种或多种、或权利要求4~7任一项所述主体材料中的一种或多种。
11.根据权利要求9或10所述的有机光电器件,其特征在于,所述有机光电器件包括有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
12.一种显示或照明装置,其特征在于,其包括如权利要求9~11任一项所述的有机光电器件。
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