CN114736180B - 芳胺类有机化合物及其用途 - Google Patents
芳胺类有机化合物及其用途 Download PDFInfo
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- CN114736180B CN114736180B CN202110017783.4A CN202110017783A CN114736180B CN 114736180 B CN114736180 B CN 114736180B CN 202110017783 A CN202110017783 A CN 202110017783A CN 114736180 B CN114736180 B CN 114736180B
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- -1 Aromatic amine organic compound Chemical class 0.000 title claims abstract description 35
- 239000000463 material Substances 0.000 claims abstract description 70
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000006413 ring segment Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 12
- 230000000903 blocking effect Effects 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000002096 quantum dot Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- MNXYJVWXMUBENA-UHFFFAOYSA-N dinaphthofuran Chemical group C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)O3)C3=CC=C21 MNXYJVWXMUBENA-UHFFFAOYSA-N 0.000 abstract description 9
- 238000009825 accumulation Methods 0.000 abstract description 3
- 125000005266 diarylamine group Chemical group 0.000 abstract description 3
- 230000009477 glass transition Effects 0.000 abstract description 3
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- 239000000543 intermediate Substances 0.000 description 72
- 230000015572 biosynthetic process Effects 0.000 description 55
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- 239000002904 solvent Substances 0.000 description 49
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 44
- 239000012074 organic phase Substances 0.000 description 41
- 229910052757 nitrogen Inorganic materials 0.000 description 40
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
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- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 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
- 238000004017 vitrification Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
本发明涉及一种芳胺类有机化合物及其用途,其中有机化合物选自如通式(1)所示的结构,按照本发明的有机化合物,将二芳胺基团与苯并二苯并呋喃基团之间加入苯环连接,并在苯并二苯并呋喃基团10位上引入一个取代或未取代的苯基基团,从而有效改善了分子的堆积,使材料分子具有更大的刚性,进而提高材料分子的玻璃化温度,以其制备发光器件,可延长器件寿命并改善器件发光效率。
Description
技术领域
本发明涉及有机电致发光技术领域,特别是涉及一种芳胺类有机化合物及其用途。
背景技术
有机电致发光现象是指利用有机物质将电能转化为光能的现象。利用有机电致发光现象的有机电致发光器件通常具有正极与负极以及在它们中间包含有机功能层的结构。为了提高有机电致发光器件的效率与寿命,有机功能层具有多层结构,每一层包含有不同的有机物质。具体的,可以包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等。在这种有机电致发光器件中,在两个电极之间施加电压,则由正极向有机功能层注入空穴,由负极向有机功能层注入电子,当注入的空穴与电子相遇时形成激子,该激子跃迁回基态时发出光。这种有机电致发光器件具有自发光、高亮度、高效率、低驱动电压、广视角、高对比度等特性,例如有机发光二极管(OLED)。OLED在光电器件(例如平板显示器和照明)的应用方面具有广视角、反应时间快、工作电压低、面板厚度薄等优势,因而具有广阔的发展潜力。
为了实现高效的有机电致发光器件,除了开发高性能的发光材料外,传输材料的开发也很重要。目前大部分传输材料都是基于咔唑类衍生物的小分子材料,此类仍然存在空穴和电子传输不平衡的缺点,致使应用此类化合物的器件寿命较短。
因此,现有技术,特别是材料解决方案还有待于改进和发展。
发明内容
鉴于上述现有技术的不足,本发明的目的在于提供一种芳胺类有机化合物、包含其的混合物,组合物、有机电子器件及应用,旨在解决现有的空穴传输材料空穴和电子传输不平衡,器件发光效率和寿命差的问题。
本发明一个方面,提供一种芳胺类有机化合物,如通式(1)所示:
其中,
R1选自苯基或联苯基或H;
R2选自苯基或萘基或H;
L1、L2分别独立选自单键或
Ar1、Ar2分别独立选自以下基团:
其中:
X选自N或CR3;
Y选自O、S、NR4、CR5R6;
R3-R6每次出现时,分别独立选自:氢原子,D,或具有1至20个C原子的直链烷基,具有3至20个C原子的支链烷基或环状的烷基,或者取代或未取代的具有5至60个环原子的芳香基团或杂芳香基团。
本发明另一个方面,提供一种混合物,包含至少一种如上所述的有机化合物,及至少一种有机功能材料,所述有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、有机发光客体材料、有机主体材料或无机量子点。
本发明的还一个方面,提供一种组合物,包含有至少一种所述的有机化合物或所述的混合物,及至少一种有机溶剂。
本发明的再一个方面,提供一种有机电子器件,包含至少一种所述的有机化合物或所述的混合物,或由所述的组合物制备而成。
与现有技术相比较,本发明具有如下有益效果:
按照本发明的有机化合物,将二芳胺基团与苯并二苯并呋喃基团之间加入苯环连接,并在苯并二苯并呋喃基团10位上引入一个取代或未取代的苯基基团,从而有效改善了分子的堆积,使材料分子具有更大的刚性,进而提高材料分子的玻璃化温度,以其制备发光器件,可延长器件寿命并改善器件发光效率。按照本发明的有机化合物可作为空穴传输材料,通过与合适的发光材料配合,能提高其作为电致发光器件的发光效率及寿命,提供了一种制造成本低、效率高、寿命长的发光器件的解决方案。
具体实施方式
以下结合具体实施例对本发明的技术方案作进一步详细的说明。本发明可以以许多不同的形式来实现,并不限于本文所描述的实施方式。相反地,提供这些实施方式的目的是使对本发明公开内容理解更加透彻全面。
除非另有定义,本文所使用的所有的技术和科学术语与属于本领域技术人员通常理解的含义相同。
本文所使用的术语“和/或”包括一个或多个相关的所列项目的任意的和所有的组合。
在本发明中,“取代”表示被取代基中的氢原子被取代基所取代。
在本发明中,同一取代基多次出现时,可独立选自不同基团。如通式含有多个R1,则R1可独立选自不同基团。
本发明中,“取代或未取代”表示所定义的基团可以被取代,也可以不被取代。当所定义的基团被取代时,应理解为任选被本领域可接受的基团所取代,包括但不限于:氘原子、氰基、异氰基、硝基、卤素原子、C1-10的烷基、C1-10的烷氧基、C1-10的烷硫基、C6-30的芳基、C6-30的芳氧基、C6-30的芳硫基、C3-30的杂芳基,C1-30的硅烷基、C2-10的烷胺基、C6-30的芳胺基,或上述基团的组合等。
在本发明中,“环原子数”表示原子键合成环状而得到的结构化合物(例如,单环化合物、稠环化合物、交联化合物、碳环化合物、杂环化合物)的构成该环自身的原子之中的原子数。该环被取代基所取代时,取代基所包含的原子不包括在成环原子内。关于以下所述的“环原子数”,在没有特别说明的条件下也是同样的。例如,苯环的环原子数为6,萘环的环原子数为10,噻吩基的环原子数为5。
在本发明中,“烷基”可以表示直链、支链和/或环状烷基。烷基的碳数可以为1至50、1至30、1至20、1至10或1至6。包含该术语的短语,例如,“C1-9烷基”是指包含1~9个碳原子的烷基,每次出现时,可以互相独立地为C1烷基、C2烷基、C3烷基、C4烷基、C5烷基、C6烷基、C7烷基、C8烷基或C9烷基。烷基的非限制性实例包括甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、2-乙基丁基、3,3-二甲基丁基、正戊基、异戊基、新戊基、叔戊基、环戊基、1-甲基戊基、3-甲基戊基、2-乙基戊基、4-甲基-2-戊基、正己基、1-甲基己基、2-乙基己基、2-丁基己基、环己基、金刚烷等。
“芳基或芳香基团”是指在芳香环化合物的基础上除去一个氢原子衍生的芳族烃基,可以为单环芳基、或稠环芳基、或多环芳基,对于多环的环种,至少一个是芳族环系。例如,“取代或未取代的具有6至40个环原子的芳基”是指包含6至40个环原子的芳基,优选取代或未取代的具有6至30个环原子的芳基,更优选取代或未取代的具有6至18个环原子的芳基,特别优选取代或未取代的具有6至14个环原子的芳基,且芳基上任选进一步被取代;合适的实例包括但不限于:苯、联苯、三联苯、萘、蒽、荧蒽、菲、苯并菲、二萘嵌苯、并四苯、芘、苯并芘、苊、芴及其衍生物。可以理解地,多个芳基也可以被短的非芳族单元间断(例如<10%的非H原子,比如C、N或O原子),具体如苊、芴,或者9,9-二芳基芴、三芳胺、二芳基醚体系也应该包含在芳基的定义中。
“杂芳基或杂芳香基团”是指在芳基的基础上至少一个碳原子被非碳原子所替代,非碳原子可以为N原子、O原子、S原子等。例如,“取代或未取代的具有5至40个环原子的杂芳基”是指具有5至40个环原子的杂芳基,,优选取代或未取代的具有6至30个环原子的杂芳基,更优选取代或未取代的具有6至18个环原子的杂芳基,特别优选取代或未取代的具有6至14个环原子的杂芳基,且杂芳基任选进一步被取代,合适的实例包括但不限于:三嗪、吡啶、嘧啶、咪唑、呋喃、噻吩、苯并呋喃、苯并噻吩、吲哚、咔唑、吡咯并咪唑、吡咯并吡咯、噻吩并吡咯、噻吩并噻吩、呋喃并吡咯、呋喃并呋喃、噻吩并呋喃、苯并异噁唑、苯并异噻唑、苯并咪唑、喹啉、异喹啉、邻二氮萘、喹喔啉、菲啶、伯啶、喹唑啉、喹唑啉酮、二苯并噻吩、二苯并呋喃、咔唑及其衍生物。
“胺基”是指胺的衍生物,具有式-N(X)2的结构特征,其中每个“X”独立地是H、取代的或未被取代的烷基、取代的或未被取代的环烷基、取代的或未被取代的杂环基等。胺基的非限制性类型包括-NH2、-N(烷基)2、-NH(烷基)、-N(环烷基)2、-NH(环烷基)、-N(杂环基)2、-NH(杂环基)、-N(芳基)2、-NH(芳基)、-N(烷基)(芳基)、-N(烷基)(杂环基)、-N(环烷基)(杂环基)、-N(芳基)(杂芳基)、-N(烷基)(杂芳基)等。
本发明中,与单键相连的“*”表示连接或稠合位点。
本发明中,基团中未指明连接位点时,表示基团中任选可连接位点作为连接位点;
本发明中,基团中未指明稠合位点时,表示基团中任选可稠合位点作为稠合位点,优选基团中处于邻位的两个或多个位点为稠合位点;
本发明中,取代基相连的单键贯穿相应的环,表述该取代基可与环的任选位置连接,例如中R与苯环的任一可取代位点相连。
在本发明中,“相邻基团”是指两个取代基之间没有可取代的位点。
本发明提供一种芳胺类有机化合物,如下通式(1)所示:
其中,
R1选自苯基或联苯基或H;
R2选自苯基或萘基或H;
L1、L2分别独立选自单键或
Ar1、Ar2分别独立选自以下基团:
其中:
X选自N或CR3;
Y选自O、S、NR4、CR5R6;
R3-R6每次出现时,分别独立选自:氢原子,D,或具有1至20个C原子的直链烷基,具有3至20个C原子的支链烷基或环状的烷基,或者取代或未取代的具有5至60个环原子的芳香基团或杂芳香基团。
在一实施例中,R3-R6每次出现时,分别独立选自:氢原子,D,或具有1至10个C原子的直链烷基,具有3至10个C原子的支链烷基或环状的烷基,或者取代或未取代的具有5至20个环原子的芳香基团或杂芳香基团。
进一步,R3-R6每次出现时,分别独立选自:氢原子,D,或具有1至8个C原子的直链烷基,具有3至8个C原子的支链烷基或环状的烷基。
在一些优选实施例中,通式(1)选自通式(2)所示的结构:
其中:R1、R2、L1、L2、Ar1和Ar2含义同上所述。
在一实施例中,R1选自苯基或H;
在一实施例中,R1选自苯基,R2选自H。
在一实施例中,R1选自H,R2选自苯基或萘基,进一步,如下通式所示:
在一实施例中,L1、L2分别独立地选自单键或苯基或萘基。
在一些实施例中,Ar1、Ar2分别独立地选自以下基团中的任一种,虚线表示连接位点:
其中:*表示连接位点。
进一步,选自如下结构:
具体地,按照本发明的化合物,优选自但不限于如下结构,这些结构可以被任意取代:
/>
其中:以上结构中的H可以进一步被任意取代。
按照本发明的芳胺类有机化合物,可以作为功能材料应用于电子器件,特别是OLED器件中。有机功能材料可分为空穴注入材料(HIM),空穴传输材料(HTM),电子传输材料(ETM),电子注入材料(EIM),电子阻挡材料(EBM),空穴阻挡材料(HBM),发光客体材料(Guest Emitter),主体材料(Host Emitter)。其中,主体材料可以分为磷光主体材料、荧光主体材料、TADF发光材料的主体材料。按照本发明的有机化合物,可以作为其中的任意一种。
在一个优先的实施例中,按照本发明的有机化合物可作为空穴传输材料。
按照本发明所述的芳胺类有机化合物,其玻璃化温度Tg≥100℃,在一个优选可选的实施例中,Tg≥120℃,在一个较为优选可选的实施例中,Tg≥140℃,在一个更为优选可选的实施例中,Tg≥160℃,在一个最为优选可选的实施例中,Tg≥180℃。
本发明还涉及一种混合物,包含有至少一种以上所述的有机化合物,及至少一种有机功能材料,所述有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、有机发光客体材料、有机主体材料或无机量子点。例如在WO2010135519A1,US20090134784A1和WO 2011110277A1中对各种有机功能材料有详细的描述,特此将此3专利文件中的全部内容并入本文作为参考。有机功能材料可以是小分子和高聚物材料。
在一实施例中,所述一种有机功能材料选自电子传输材料,与本发明所述的有机化合物共混作为共主体运用于电子器件中。
本发明的一个目的是为蒸镀型OLED提供材料解决方案。
在某些实施例中,按照本发明的有机化合物,其分子量≤1100g/mol,优选≤1000g/mol,很优选≤950g/mol,更优选≤900g/mol,最优选≤800g/mol。
本发明的另一个目的是为印刷OLED提供材料解决方案。
在某些实施例中,按照本发明的有机化合物,其分子量≥700g/mol,优选≥900g/mol,优选≥1000g/mol,最优选≥1100g/mol。
本发明还涉及一种组合物,包含有至少一种所述的有机化合物或如所述的混合物,及至少一种有机溶剂。
所述有机溶剂可以选自芳族或杂芳族、酯、芳族酮或芳族醚、脂肪族酮或脂肪族醚、脂环族或烯烃类化合物,或硼酸酯或磷酸酯类化合物中的任意一种,或两种及两种以上溶剂的混合物。优选地,所述有机溶剂选自基于芳族或杂芳族的溶剂。
适合本发明的基于芳族或杂芳族溶剂的例子有,但不限制于:对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、环己基苯、苄基丁基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-三氯苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、N-甲基二苯胺、4-异丙基联苯、α,α-二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘、喹啉、异喹啉、2-呋喃甲酸甲酯、2-呋喃甲酸乙酯等。
适合本发明的基于芳族酮溶剂的例子有,但不限制于:1-四氢萘酮,2-四氢萘酮,2-(苯基环氧)四氢萘酮,6-(甲氧基)四氢萘酮,苯乙酮、苯丙酮、二苯甲酮、及它们的衍生物,如4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮、2-甲基苯丙酮等。
适合本发明的基于芳族醚溶剂的例子有,但不限制于:3-苯氧基甲苯、丁氧基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本乙醚、1,3-二丙氧基苯、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚等。
适合本发明的基于脂肪族酮或脂肪族醚溶剂的例子有,但不限制于:2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、葑酮、佛尔酮、异佛尔酮、二正戊基酮,戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚等。
适合本发明的基于硼酸酯或磷酸酯溶剂的例子有,但不限制于:辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯、油酸烷酯等。特别优选辛酸辛酯、癸二酸二乙酯、邻苯二甲酸二烯丙酯、异壬酸异壬酯。
在某些优选的实施例中,按照本发明的一种组合物,可以包含至少一种如上所述的有机化合物或高聚物或混合物,至少一种有机溶剂以及至少一种助溶剂。所述助溶剂的例子包括(但不限于):甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷、茚和/或它们的混合物。
一些优选的实施例中,特别适合本发明的溶剂是汉森(Hansen)溶解度参数在以下范围内的溶剂:δd(色散力)在17.0~23.2MPa1/2的范围,尤其是在18.5~21.0MPa1/2的范围;δp(极性力)在0.2~12.5MPa1/2的范围,尤其是在2.0~6.0MPa1/2的范围;δh(氢键力)在0.9~14.2MPa1/2的范围,尤其是在2.0~6.0MPa1/2的范围。
按照本发明的组合物,其中有机溶剂在选取时需考虑其沸点参数。本发明中,所述有机溶剂的沸点≥150℃;优选为≥180℃;较优选为≥200℃;更优为≥250℃;最优为≥275℃或≥300℃。这些范围内的沸点对防止喷墨印刷头的喷嘴堵塞是有益的。所述有机溶剂可从溶剂体系中蒸发,以形成包含有机功能材料的薄膜。
在一实施方案中,按照本发明的组合物是一溶液。在另一实施方案中,按照本发明的组合物是一悬浮液。
本发明实施例中的组合物中可以包括0.01至10wt%的按照本发明的有机化合物或其混合物,较好的是0.1至15wt%,更好的是0.2至5wt%,最好的是0.25至3wt%。
本发明还涉及所述组合物作为涂料或印刷油墨在制备有机电子器件时的用途,特别优选的是通过打印或涂布的制备方法。
其中,适合的打印或涂布技术包括(但不限于)喷墨打印,喷印(NozzlePrinting),活版印刷,丝网印刷,浸涂,旋转涂布,刮刀涂布,辊筒印花,扭转辊印刷,平版印刷,柔版印刷,轮转印刷,喷涂,刷涂或移印,狭缝型挤压式涂布等。首选的是凹版印刷,喷印及喷墨印刷。溶液或悬浮液可以另外包括一个或多个组份例如表面活性化合物,润滑剂,润湿剂,分散剂,疏水剂,粘接剂等,用于调节粘度,成膜性能,提高附着性等。有关打印技术,及其对有关溶液的相关要求,如溶剂及浓度,粘度等。
本发明进一步涉及一种如上所述的芳胺类有机化合物、混合物或组合物在有机电子器件中的应用。本发明实施例中,优选将所述有机化合物用于OLED器件的空穴传输层。
本发明更进一步涉及一种有机电子器件,包含两个电极,设置在所述两个电极之间的一个或多个有机功能层,所述有机功能层包含如上所述的芳胺类有机化合物、混合物或由上述的组合物制备而成。进一步地,所述有机电子器件,包含阴极、阳极和位于阴极和阳极的一个或多个有机功能层。
阳极可包含一导电金属或金属氧化物,或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)或空穴传输层(HTL)或发光层中。在一个的实施例中,阳极的功函数和发光层中的发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。阳极材料的例子包含但不限于:Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。其他合适的阳极材料是已知的,本领域普通技术人员可容易地选择使用。阳极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包含射频磁控溅射,真空热蒸发,电子束(e-beam)等。在某些实施例中,阳极是图案结构化的。图案化的ITO导电基板可在市场上买到,并且可以用来制备根据本发明申请的器件。
阴极可包含一导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一个实施例中,阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。原则上,所有可用作OLED的阴极的材料都可能作为本发明申请器件的阴极材料。阴极材料的例子包含但不限于:Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包含射频磁控溅射,真空热蒸发,电子束(e-beam)等。
在一些实施例中,按照本发明的有机电致发光器件,其中包括一个或者更多个有机功能层,所述的有机功能层选自电子注入层、电子传输层、空穴阻挡层、空穴注入层、空穴传输层、电子阻挡层和发光层的一个或多个层,其中至少包含一个发光层和一个空穴传输层。适合用于这些功能层中的材料上所述,在此不再赘述。
在一些实施例中,按照本发明的有机电致发光器件,所述发光层中的发光材料选自单重态发光体、三重态发光体或者TADF材料。
在一些更为可选的实施例中,按照本发明的有机电致发光器件,一般有机功能层的厚度为10nm至200nm,较好为20nm至150nm,更好为30nm至100nm,最好为40nm至90nm。
所述有机电子器件可选自,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic Plasmon EmittingDiode)等,特别优选的是有机电致发光器件,如OLED,OLEEC,有机发光场效应管。
本发明还涉及按照本发明的电致发光器件在各种电子设备中的应用,包含,但不限于,显示设备,照明设备,光源,传感器等等。
本发明还涉及包含有按照本发明的有机电子器件的电子设备,包括,但不限于,显示设备,照明设备,光源,传感器等等。
下面将结合优选实施例对本发明进行了说明,但本发明并不局限于下述实施例,应当理解,所附权利要求概括了本发明的范围在本发明构思的引导下本领域的技术人员应意识到,对本发明的各实施例进行的一定的改变,都将被本发明的权利要求书的精神和范围所覆盖。
具体实施例
按照本发明的化合物的合成方法举例,但本发明并不局限于下述实施例。
实施例1化合物C-1的合成
中间体1-3的合成:
将中间体1-1(10mmol)、中间体1-2(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体1-3摩尔量为5.46mmol,产率:54.6%。MS(ASAP)=254.1
中间体1-4的合成:
将化合物1-3(10mmol)、五氧化二磷(30mmol)和30mL三氟甲磺酸加入到100mL三口瓶中,室温搅拌24小时,结束反应,将反应液缓慢倒置300冰水中,抽滤,滤渣先后用水、碳酸氢钠水溶液、水冲洗数遍,收集滤渣,烘干后将其置于50mL的吡啶中,回流反应12小时,冷却到室温后,用二氯甲烷萃取3遍,有机相柱层析并重结晶得到中间体1-4摩尔量为7.22mmol,产率:72.2%。MS(ASAP)=252.1
中间体1-6的合成:
将中间体1-4(10mmol)、中间体1-5(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体1-6摩尔量为6.24mmol,产率:62.4%。MS(ASAP)=294.1
中间体1-7的合成:
250ml的三口烧瓶中加入10mmol中间体1-6以及100ml干燥甲苯,在N2气氛中,冷却至-30摄氏度,逐滴加入(30.6mmol)n-BuLi正已烷溶液。升高温度至60摄氏度反应2小时,减压蒸除其中的正已烷溶剂。将反应液再次冷却至-30摄氏度,加入21mol碘单质,升至室温下搅拌0.5小时,将反应液冷却至室温。加入碳酸钠水溶液与乙酸乙酯淬灭反应。水相用乙酸乙酯萃取并合并有机相,旋蒸掉其中的溶剂,得到粗品,用快速硅胶柱纯化得到纯品。用甲苯与乙酸乙酯重结晶,得到中间体1-7摩尔量为5.31mmol,产率:53.1%。MS(ASAP)=420.3化合物C-1的合成:将化合物1-7(10mmol)、化合物1-8(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-1,产率:48.3%。MS(ASAP)=689.3
实施例2化合物C-2的合成
中间体2-2的合成:
将中间体1-7(10mmol)、中间体2-1(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体2-2摩尔量为8.47mmol,产率:84.7%。MS(ASAP)=448.0
中间体2-4的合成:
将化合物2-2(10mmol)、化合物2-3(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到中间体2-4摩尔量为7.17mmol,产率:71.7%。MS(ASAP)=537.2
化合物C-2的合成:
将化合物2-4(10mmol)、化合物2-5(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-2,产率:63.3%。MS(ASAP)=729.3
实施例3化合物C-3的合成
中间体3-2的合成:
将化合物2-2(10mmol)、化合物3-1(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到中间体3-2摩尔量为9.11mmol,产率:91.1%。MS(ASAP)=543.1
化合物C-3的合成:
将化合物3-2(10mmol)、化合物3-3(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-3,产率:51.6%。MS(ASAP)=735.6
实施例4化合物C-4的合成
中间体4-2的合成:
将中间体1-4(10mmol)、中间体4-1(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体4-2摩尔量为8.63mmol,产率:86.3%。MS(ASAP)=370.1
中间体4-3的合成:
250ml的三口烧瓶中加入10mmol中间体4-2以及100ml干燥甲苯,在N2气氛中,冷却至-30摄氏度,逐滴加入(30.6mmol)n-BuLi正已烷溶液。升高温度至60摄氏度反应2小时,减压蒸除其中的正已烷溶剂。将反应液再次冷却至-30摄氏度,加入21mol碘单质,升至室温下搅拌0.5小时,将反应液冷却至室温。加入碳酸钠水溶液与乙酸乙酯淬灭反应。水相用乙酸乙酯萃取并合并有机相,旋蒸掉其中的溶剂,得到粗品,用快速硅胶柱纯化得到纯品。用甲苯与乙酸乙酯重结晶,得到中间体4-3摩尔量为7.64mmol,产率:76.4%。MS(ASAP)=496.2
化合物C-4的合成:将化合物4-3(10mmol)、化合物4-4(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-4,产率:64.8%。MS(ASAP)=613.2
实施例5化合物C-5的合成
中间体5-2的合成:
将中间体1-7(10mmol)、中间体5-1(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体5-2摩尔量为5.44mmol,产率:54.4%。MS(ASAP)=573.9
中间体5-4的合成:
将中间体5-2(10mmol)、中间体5-3(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体5-4摩尔量为8.97mmol,产率:89.7%。MS(ASAP)=524.1
化合物C-5的合成:
将化合物5-4(10mmol)、化合物5-5(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-5,产率:49.3%。MS(ASAP)=613.2
实施例6化合物C-6的合成
中间体6-2的合成:
将中间体1-7(10mmol)、中间体6-1(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体6-2摩尔量为7.64mmol,产率:76.4%。MS(ASAP)=573.1
中间体6-4的合成:
将中间体6-2(10mmol)、中间体6-3(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体6-4摩尔量为5.69mmol,产率:56.9%。MS(ASAP)=574.6
化合物C-6的合成:
将化合物6-4(10mmol)、化合物6-5(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-6,产率:87.2%。MS(ASAP)=815.2
实施例7化合物C-7的合成
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化合物C-7的合成:
将化合物2-4(10mmol)、化合物7-1(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-7,产率:81.4%。MS(ASAP)=739.3
实施例8化合物C-8的合成
中间体8-2的合成:
将化合物2-2(10mmol)、化合物8-1(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到中间体8-2摩尔量为7.54mmol,产率:75.4%。MS(ASAP)=626.2
化合物C-8的合成:
将化合物8-2(10mmol)、化合物8-3(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-8,产率:78.6%。MS(ASAP)=867.3
实施例9化合物C-9的合成
中间体9-2的合成:
将中间体1-7(10mmol)、中间体9-1(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体9-2摩尔量为8.34mmol,产率:83.4%。MS(ASAP)=448.0
中间体9-4的合成:
将化合物9-2(10mmol)、化合物9-3(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到中间体9-4摩尔量为8.66mmol,产率:86.6%。MS(ASAP)=461.2
化合物C-9的合成:
将化合物9-4(10mmol)、化合物9-5(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-9,产率:71.4%。MS(ASAP)=613.4
实施例10化合物C-10的合成
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中间体10-2的合成:
将中间体4-3(10mmol)、中间体10-1(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体10-2摩尔量为6.97mmol,产率:69.7%。MS(ASAP)=524.0
中间体10-4的合成:
将化合物10-2(10mmol)、化合物10-3(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到中间体10-4摩尔量为8.14mmol,产率:81.4%。MS(ASAP)=613.2
化合物C-10的合成:
将化合物10-4(10mmol)、化合物10-5(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-10,产率:65.2%。MS(ASAP)=779.6
实施例11化合物C-11的合成
化合物C-11的合成:
将化合物10-2(10mmol)、化合物11-1(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-11,产率:87.9%。MS(ASAP)=865.3
实施例12化合物C-12的合成
化合物C-12的合成:
将化合物5-4(10mmol)、化合物12-1(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-12,产率:62.3%。MS(ASAP)=965.3
实施例13化合物C-13的合成
中间体13-2的合成:
将化合物5-4(10mmol)、化合物13-1(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到中间体13-2摩尔量为7.05mmol,产率:70.5%。MS(ASAP)=613.1
化合物C-13的合成:
将化合物13-2(10mmol)、化合物13-3(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-13,产率:54.6%。MS(ASAP)=865.3
实施例14化合物C-14的合成
化合物C-14的合成:
将化合物5-4(10mmol)、化合物14-1(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-14,产率:86.1%。MS(ASAP)=845.8
实施例15化合物C-15的合成
中间体15-2的合成:
将中间体5-2(10mmol)、中间体15-1(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1mmol)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体15-2摩尔量为8.35mmol,产率:83.5%。MS(ASAP)=574.0
中间体15-4的合成:
将化合物15-2(10mmol)、化合物15-3(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到中间体15-4摩尔量为7.46mmol,产率:74.6%。MS(ASAP)=663.5
化合物C-15的合成:
将化合物15-4(10mmol)、化合物15-5(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-15,产率:51.7%。MS(ASAP)=845.2
实施例16化合物C-16的合成
中间体16-2的合成:
将中间体5-2(10mmol)、中间体16-1(10mmol)溶于1,4-二氧六环与水(21/2ml)的混合溶剂中,并加入Pd(PPh3)4(0.1)和碳酸钾(30mmol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到中间体16-2摩尔量为7.18mmol,产率:71.8%。MS(ASAP)=574.0
中间体16-4的合成:
将化合物16-2(10mmol)、化合物16-3(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到中间体16-4摩尔量为5.98mmol,产率:59.8%。MS(ASAP)=663.5
化合物C-16的合成:
将化合物16-4(10mmol)、化合物16-5(10mmol)、Pd(dba)2(0.1mmol)、TTBP(0.2mmol)和叔丁醇钠(30mmol)溶于甲苯中,在氮气气氛下100℃搅拌6h。冷却后旋蒸除去溶剂,萃取并水洗分液,有机相柱层析得到化合物C-16,产率:47.6%。MS(ASAP)=904.3
化合物的能级
有机化合物能级计算
有机化合物材料的能级可通过量子计算得到,比如利用TD-DFT(含时密度泛函理论)通过Gaussian09W(Gaussian Inc.),具体的模拟方法可参见WO2011141110。首先用半经验方法“Ground State/Semi-empirical/Default Spin/AM1”(Charge 0/Spin Singlet)来优化分子几何结构,然后有机分子的能量结构由TD-DFT(含时密度泛函理论)方法算得“TD-SCF/DFT/Default Spin/B3PW91”与基组“6-31G(d)”(Charge 0/Spin Singlet)。HOMO和LUMO能级按照下面的校准公式计算,S1,T1和谐振因子f(S1)直接使用。
HOMO(eV)=((HOMO(G)×27.212)-0.9899)/1.1206
LUMO(eV)=((LUMO(G)×27.212)-2.0041)/1.385
其中HOMO(G)和LUMO(G)是Gaussian 09W的直接计算结果,单位为Hartree。结果如表1所示:
表1材料的分子计算结果
实施例化合物1-化合物16的ET1和ES1能级均略高于化合物Ref-1-Ref-5,特别是Ref-5的ET1和ES1能级均明显低于实施例化合物0.2eV左右。
OLED器件的制备及表征
下面通过具体实施例来详细说明采用上述的OLED器件的制备过程,OLED器件的结构为:ITO/HIL(10nm)/HT-1(60nm)/HT-2(60nm)/BH:BD(25nm)/ET:Liq(30nm)/Liq(1nm)/Al(100nm),制备步骤如下:
a、导电玻璃基片的清洗:使用氯仿、酮、异丙醇进行清洗,然后进行紫外臭氧等离子处理;
b、功能层制备:将ITO基片移入真空气相沉积设备中,在高真空(1×10-6毫巴)下,采用电阻加热蒸发,HATCN蒸镀形成10nm的注入层(HIL),之后依次蒸镀得到60nm的第一空穴传输层(HT-1)以及60nm的第二空穴传输层(本发明化合物以及对比化合物)。随后BH和BD以重量比97:3的比例共蒸镀形成25nm的发光层。接着将ET和LiQ置于不同的蒸发单元,使其分别以50重量%的比例进行共沉积,在发光层上形成30nm的电子传输层,随后在电子传输层上沉积1nm的LiQ作为电子注入层,最后在所述电子注入层上沉积厚度为100nm的Al阴极;
c、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
所有器件除第二空穴传输层材料换成实施例所示化合物,其他实施方案均相同。各OLED器件的电流电压(J-V)特性通过表征设备来表征,同时记录重要的参数如效率,寿命及外部量子效率。经检测,采用化合物1~化合物16作为第二空穴传输层材料即HT-2,所得到器件的效率和寿命相比对比化合物都有提高,详情见表2。
器件中所涉及的化合物结构如下:
表2
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各OLED器件的电流电压(J-V)特性通过表征设备来表征,同时记录重要的参数如电压,寿命及外部量子效率。表2是OLED器件寿命及外量子效率比较,其中的寿命LT95是在恒定电流下,亮度下降到初始亮度@1000nits的95%时的时间。这里LT95、外量子效率是相对于对比器件实施例1而计算的,即以对比器件实施例1的寿命为1,外量子效率为100%。
器件实施例1~实施例16的器件外量子效率和寿命明显高于对比器件实施例1~对比器件实施例5,其原因可能在于:
二芳胺与苯并二苯并呋喃基团间,以及在苯并二苯并呋喃基团10位上,均引入取代或未取代的苯基基团,使分子的空间结构相对于对比例分子有较大改变,从而改善了分子的堆积,使分子具有较大的刚性,同时提高了分子的玻璃化温度,增加了器件的效率、稳定性和寿命。
器件实施例1-实施例16的器件外量子效率和寿命明显高于对比器件实施例5,其原因可能在于:
引入1个苯并二苯并呋喃基团比引入2个苯并二苯并呋喃基团更能增加器件的效率、稳定性和寿命,这是因为引入2个苯并二苯并呋喃基团使得分子结构发生钝化,同时分子量过大不利于空穴传输,导致器件的效率、稳定性和寿命均有所下降。
基于本发明的空穴传输材料明显优于对比实施例所示空穴传输材料。可见,采用本发明的有机混合物制备的OLED器件,其发光效率和寿命均得到明显提高。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (9)
1.一种芳胺类有机化合物,如通式(1)所示:
其中,
R1选自苯基或联苯基或H;
R2选自苯基或萘基或H;
L1、L2分别独立选自单键、苯基或萘基;
Ar1、Ar2分别独立选自以下基团:
其中:
X选自CR3;
Y选自O、S、NR4、CR5R6;
R3选自氢原子或具有3至10个C原子的环状的烷基;
R4-R6每次出现时,分别独立选自:具有1至10个C原子的直链烷基、具有3至10个C原子的支链烷基,或者具有6至14个环原子的芳基。
2.根据权利要求1所述的有机化合物,其特征在于,通式(1)选自通式(2)所示的结构:
3.根据权利要求1或2所述的有机化合物,其特征在于,通式(1)选自通式(3-1)或通式(3-2):
4.根据权利要求1-3任一项所述的有机化合物,其特征在于,Ar1、Ar2分别独立地选自以下基团中的任一种:
其中:*表示连接位点。
5.根据权利要求1-3任一项所述的有机化合物,其特征在于,选自如下结构:
6.根据权利要求1所述的有机化合物,其特征在于,所述有机化合物选自如下结构:
7.一种混合物,其特征在于,包含至少一种如权利要求1~6任一项所述的有机化合物,及至少一种有机功能材料,所述有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、有机发光客体材料、有机主体材料和无机量子点。
8.一种组合物,其特征在于,包含有至少一种如权利要求1~6任一项所述的有机化合物或如权利要求7所述的混合物,及至少一种有机溶剂。
9.一种有机电子器件,包含至少一种如权利要求1~6任一项所述的有机化合物或如权利要求7所述的混合物,或由权利要求8所述的组合物制备而成。
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