CN112209802A - 有机电致发光化合物和包含其的有机电致发光装置 - Google Patents
有机电致发光化合物和包含其的有机电致发光装置 Download PDFInfo
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- CN112209802A CN112209802A CN202010559242.XA CN202010559242A CN112209802A CN 112209802 A CN112209802 A CN 112209802A CN 202010559242 A CN202010559242 A CN 202010559242A CN 112209802 A CN112209802 A CN 112209802A
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- 125000003118 aryl group Chemical group 0.000 claims description 55
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- 229910052805 deuterium Inorganic materials 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000005104 aryl silyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 3
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- 238000003747 Grignard reaction Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C07D277/62—Benzothiazoles
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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Abstract
本公开涉及一种有机电致发光化合物以及一种包含其的有机电致发光装置。通过包含根据本公开的有机电致发光化合物可以提供具有改善的驱动电压和/或电流效率特征的有机电致发光装置。
Description
技术领域
本公开涉及一种有机电致发光化合物以及一种包含其的有机电致发光装置。
背景技术
电致发光(EL)装置是一种自发光装置,其具有的优点在于它提供更宽的视角、更大的对比率和更快的响应时间。有机EL装置首先是由伊士曼柯达公司(Eastman Kodak)于1987年通过使用小的芳香族二胺分子和铝络合物作为用于形成发光层的材料而开发的[Appl.Phys.Lett.[应用物理学快报]51,913,1987]。
有机电致发光装置(OLED)通过向有机发光材料施加电力而将电能转换为光,并且通常包括阳极、阴极和在这两个电极之间形成的有机层。OLED的有机层可以包括空穴注入层、空穴传输层、空穴辅助层、发光辅助层、电子阻挡层、发光层(含有主体和掺杂剂材料)、电子缓冲层、空穴阻挡层、电子传输层、电子注入层等。有机层中使用的材料可以根据功能分为空穴注入材料、空穴传输材料、空穴辅助材料、发光辅助材料、电子阻挡材料、发光材料、电子缓冲材料、空穴阻挡材料、电子传输材料、电子注入材料等。在OLED中,由于施加电压,将空穴从阳极注入发光层,将电子从阴极注入发光层,并且高能量的激子是通过空穴和电子的再结合而形成。通过此能量,有机发光化合物达到激发态,并且通过从由于所述有机发光化合物的激发态恢复到基态的能量发射光而发生发光。
最近,根据显示器的较大面积,需要可以展现出更精美且鲜艳的颜色的发光材料。具体地,在发射蓝光的材料的情况下,材料如ADN和DPVBi用作主体材料,并且材料如基于芳香族胺的化合物、铜酞菁化合物、基于咔唑的衍生物、基于苝的衍生物、基于香豆素的衍生物和基于芘的衍生物用作掺杂剂材料。然而,这些材料难以获得具有高颜色纯度的深蓝色,并且由于随着波长变得更短具有更差的电流效率是有问题的。
因此,在实现全色显示器方面,需要开发具有优异的电流效率的深蓝色的发光材料和具有与发射蓝光的材料相匹配的能级的其他有机材料。
韩国专利号1423070公开了一种包含蒽部分的有机电致发光化合物。然而,此参考文献没有具体地公开本公开的包含芳香族部分(其中联苯和萘稠合)的有机电致发光化合物。
发明内容
技术问题
本公开的目的是首先提供一种有效生产具有低驱动电压和/或高电流效率特征的有机电致发光装置的有机电致发光化合物。第二是提供一种包含所述有机电致发光化合物的有机电致发光装置。
问题的解决方案
迄今为止通常使用的发射蓝光的有机电致发光装置具有比发射绿光和红光的有机电致发光装置更低的电流效率。这是因为发射蓝光的有机电致发光装置使用荧光掺杂剂。荧光材料的能量转移机理遵循能量转移。在能量转移中,主体的发光在激发掺杂剂时是重要的。即,随着主体的发光增加,有机电致发光装置的电流效率增加。为了增加主体的发光,通常需要减少主体发光的猝灭,并且认为主体发光的猝灭是由于主体的堆叠。本发明的诸位发明人在研究后引入了庞大的芳香族部分(其中联苯和萘稠合)作为取代基以便阻碍主体的堆叠。结果是,确认提高了蓝色有机电致发光装置的电流效率。此外,据信因为本公开的芳香族部分(其中联苯和萘稠合)包含萘结构,其在发光方面是优异的,所以可以更有效地增加发射蓝光的有机电致发光装置的电流效率。具体地,本发明的诸位发明人通过发现由下式1表示的有机电致发光化合物实现上述目的已经完成了本发明。
其中
Ar1表示取代或未取代的(C6-C30)芳基、或取代或未取代的(5元至30元)杂芳基;
R5和R6各自独立地表示氢、氘、卤素、氰基、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的(5元至30元)杂芳基;
其中Ar2在位置R1至R4之一处连接至(*表示与Ar2连接的位置),并且不与连接的R1至R4各自独立地表示氢、氘、卤素、氰基、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的(5元-30元)杂芳基;
a和d各自独立地表示1至3的整数,并且b、c、e和f各自独立地表示1至4的整数;
其中如果a至f是2或更大的整数,则每个R1至每个R6可以彼此相同或不同。
本发明的有益效果
通过使用根据本公开的有机电致发光化合物,可以生产具有改善的驱动电压和/或电流效率特征的有机电致发光装置。
具体实施方式
在下文中,将详细描述本公开。然而,以下描述旨在解释本发明,并不意味着以任何方式限制本发明的范围。
本公开中的术语“有机电致发光化合物”意指可以用于有机电致发光装置中并且如有需要可以包含在构成有机电致发光装置的任何层中的化合物。
本公开中的术语“有机电致发光材料”意指可以用于有机电致发光装置中并且可以包含至少一种化合物的材料。如有需要,有机电致发光材料可以包含在构成有机电致发光装置的任何层中。例如,有机电致发光材料可以是空穴注入材料、空穴传输材料、空穴辅助材料、发光辅助材料、电子阻挡材料、发光材料、电子缓冲材料、空穴阻挡材料、电子传输材料、电子注入材料等。
本公开的有机电致发光材料可以包含至少一种由式1表示的化合物。由式1表示的化合物可以包含在发光层中,但不限于此。当包含在发光层中时,由式1表示的化合物可以作为主体如用于发射蓝光的主体被包含。根据本公开的一个实施例,具有式1的化合物可以是荧光主体,例如用于发射蓝光的荧光主体。
在下文中,将更详细地描述由式1表示的化合物。
在本文中,术语“(C1-C30)烷基”意指具有1至30个构成链的碳原子的直链或支链烷基,其中碳原子的数目优选地是1至20,并且更优选地是1至10。上述烷基可以包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基等。术语“(C2-C30)烯基”意指具有2至30个构成链的碳原子的直链或支链烯基,其中碳原子的数目优选地是2至20,并且更优选地是2至10。上述烯基可以包括乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等。术语“(C2-C30)炔基”意指具有2至30个构成链的碳原子的直链或支链炔基,其中碳原子的数目优选地是2至20,并且更优选地是2至10。上述炔基可以包括乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等。术语“(C3-C30)环烷基”意指具有3至30个环骨架碳原子的单环烃或多环烃,其中碳原子的数目优选地是3至20,并且更优选地是3至7。上述环烷基可以包括环丙基、环丁基、环戊基、环己基等。术语“(3元至7元)杂环烷基”意指具有3至7个、优选地5至7个环骨架原子并且包含至少一个杂原子的环烷基,所述杂原子选自由B、N、O、S、Si和P组成的组,优选地由O、S和N组成的组。上述杂环烷基可以包括四氢呋喃、吡咯烷、四氢噻吩(thiolan)、四氢吡喃等。术语“(C6-C30)芳基”意指衍生自具有6至30个环骨架碳原子的芳香族烃的单环或稠环基团,其中环骨架碳原子的数目优选地是6至25个,更优选地是6至18个。上述芳基可以是部分饱和的,并且可以包含螺结构。上述芳基可以包括苯基、联苯基、三联苯基、萘基、联萘基、苯基萘基、萘基苯基、苯基三联苯基、芴基、苯基芴基、苯并芴基、二苯并芴基、菲基、苯基菲基、蒽基、茚基、三亚苯基、芘基、并四苯基、苝基、基、萘并萘基(naphthacenyl)、荧蒽基、螺二芴基、薁基等。更具体地,所述芳基可以包括苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、苯并蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基、萘并萘基、芘基、1-基、2-基、3-基、4-基、5-基、6-基、苯并[c]菲基、苯并[g]基、1-三亚苯基、2-三亚苯基、3-三亚苯基、4-三亚苯基、1-芴基、2-芴基、3-芴基、4-芴基、9-芴基、苯并芴基、二苯并芴基、2-联苯基、3-联苯基、4-联苯基、邻三联苯基、间三联苯-4-基、间三联苯-3-基、间三联苯-2-基、对三联苯-4-基、对三联苯-3-基、对三联苯-2-基、间四联苯基、3-荧蒽基、4-荧蒽基、8-荧蒽基、9-荧蒽基、苯并荧蒽基、邻甲苯基、间甲苯基、对甲苯基、2,3-二甲苯基、3,4-二甲苯基、2,5-二甲苯基、均三甲苯基、邻异丙苯基、间异丙苯基、对异丙苯基、对叔丁基苯基、对(2-苯基丙基)苯基、4'-甲基联苯基、4"-叔丁基-对三联苯-4-基、9,9-二甲基-1-芴基、9,9-二甲基-2-芴基、9,9-二甲基-3-芴基、9,9-二甲基-4-芴基、9,9-二苯基-1-芴基、9,9-二苯基-2-芴基、9,9-二苯基-3-芴基、9,9-二苯基-4-芴基等。
在本文中,术语“(3元至30元)杂芳基”是具有3至30个环骨架原子并且包括至少一个、优选地1至4个选自由B、N、O、S、Si和P组成的组的杂原子的芳基。上述杂芳基可以是单环、或与至少一个苯环缩合的稠环;可以是部分饱和的;可以是通过经由一个或多个单键将至少一个杂芳基或芳基连接至杂芳基而形成的杂芳基;并且可以包含螺旋结构。上述杂芳基可以包括单环型杂芳基,如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、***基、四唑基、呋咱基、吡啶基、吡嗪基、嘧啶基、哒嗪基等,以及稠环型杂芳基,如苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并萘并呋喃基、苯并萘并噻吩基、苯并咪唑基、苯并噻唑基、萘并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、苯并吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、苯并喹唑啉基、喹喔啉基、苯并喹喔啉基、萘啶基、咔唑基、苯并咔唑基、二苯并咔唑基、吩噁嗪基、吩噻嗪基、菲啶基、苯并二氧杂环戊烯基、二氢吖啶基等。更具体地,所述杂芳基可以包括1-吡咯基、2-吡咯基、3-吡咯基、吡嗪基、2-吡啶基、2-嘧啶基、4-嘧啶基、5-嘧啶基、6-嘧啶基、1,2,3-三嗪-4-基、1,2,4-三嗪-3-基、1,3,5-三嗪-2-基、1-咪唑基、2-咪唑基、1-吡唑基、1-吲哚啉基、2-吲哚啉基、3-吲哚啉基、5-吲哚啉基、6-吲哚啉基、7-吲哚啉基、8-吲哚啉基、2-咪唑并吡啶基、3-咪唑并吡啶基、5-咪唑并吡啶基、6-咪唑并吡啶基、7-咪唑并吡啶基、8-咪唑并吡啶基、3-吡啶基、4-吡啶基、1-吲哚基、2-吲哚基、3-吲哚基、4-吲哚基、5-吲哚基、6-吲哚基、7-吲哚基、1-异吲哚基、2-异吲哚基、3-异吲哚基、4-异吲哚基、5-异吲哚基、6-异吲哚基、7-异吲哚基、2-呋喃基、3-呋喃基、2-苯并呋喃基、3-苯并呋喃基、4-苯并呋喃基、5-苯并呋喃基、6-苯并呋喃基、7-苯并呋喃基、1-异苯并呋喃基、3-异苯并呋喃基、4-异苯并呋喃基、5-异苯并呋喃基、6-异苯并呋喃基、7-异苯并呋喃基、2-喹啉基、3-喹啉基、4-喹啉基、5-喹啉基、6-喹啉基、7-喹啉基、8-喹啉基、1-异喹啉基、3-异喹啉基、4-异喹啉基、5-异喹啉基、6-异喹啉基、7-异喹啉基、8-异喹啉基、2-喹喔啉基、5-喹喔啉基、6-喹喔啉基、1-咔唑基、2-咔唑基、3-咔唑基、4-咔唑基、9-咔唑基、氮杂咔唑基-1-基、氮杂咔唑基-2-基、氮杂咔唑基-3-基、氮杂咔唑基-4-基、氮杂咔唑基-5-基、氮杂咔唑基-6-基、氮杂咔唑基-7-基、氮杂咔唑基-8-基、氮杂咔唑基-9-基、1-菲啶基、2-菲啶基、3-菲啶基、4-菲啶基、6-菲啶基、7-菲啶基、8-菲啶基、9-菲啶基、10-菲啶基、1-吖啶基、2-吖啶基、3-吖啶基、4-吖啶基、9-吖啶基、2-噁唑基、4-噁唑基、5-噁唑基、2-噁二唑基、5-噁二唑基、3-呋咱基、2-噻吩基、3-噻吩基、2-甲基吡咯-1-基、2-甲基吡咯-3-基、2-甲基吡咯-4-基、2-甲基吡咯-5-基、3-甲基吡咯-1-基、3-甲基吡咯-2-基、3-甲基吡咯-4-基、3-甲基吡咯-5-基、2-叔丁基吡咯-4-基、3-(2-苯基丙基)吡咯-1-基、2-甲基-1-吲哚基、4-甲基-1-吲哚基、2-甲基-3-吲哚基、4-甲基-3-吲哚基、2-叔丁基-1-吲哚基、4-叔丁基-1-吲哚基、2-叔丁基-3-吲哚基、4-叔丁基-3-吲哚基、1-二苯并呋喃基、2-二苯并呋喃基、3-二苯并呋喃基、4-二苯并呋喃基、1-二苯并噻吩基、2-二苯并噻吩基、3-二苯并噻吩基、4-二苯并噻吩基、1-硅芴基、2-硅芴基、3-硅芴基、4-硅芴基、1-锗芴基、2-锗芴基、3-锗芴基、4-锗芴基等。“卤素”包括F、Cl、Br和I。
此外,“邻位(o-)”、“间位(m-)”、和“对位(p-)”是前缀,分别表示取代基的相对位置。邻位表示两个取代基彼此相邻,并且例如当苯衍生物中的两个取代基占据位置1和2时,被称为邻位。间位表示两个取代基在位置1和3处,并且例如当苯衍生物中的两个取代基占据位置1和3时,被称为间位。对位表示两个取代基在位置1和4处,并且例如当苯衍生物中的两个取代基占据位置1和4时,被称为对位。
在本文中,表述“取代或未取代的”中的“取代的”意指某个官能团中的氢原子被另一个原子或另一个官能团(即,取代基)替代。在R1至R6和Ar1中,取代的烷基、取代的芳基和取代的杂芳基的取代基各自独立地是选自由以下组成的组的至少一个:氘;卤素;氰基;羧基;硝基;羟基;(C1-C30)烷基;卤代(C1-C30)烷基;(C2-C30)烯基;(C2-C30)炔基;(C1-C30)烷氧基;(C1-C30)烷硫基;(C3-C30)环烷基;(C3-C30)环烯基;(3元至7元)杂环烷基;(C6-C30)芳氧基;(C6-C30)芳硫基;未取代的或被一个或多个(C6-C30)芳基取代的(3元至30元)杂芳基;未取代的或被氘、一个或多个(C1-C30)烷基和一个或多个(3元至30元)杂芳基中的至少一个取代的(C6-C30)芳基;三(C1-C30)烷基甲硅烷基;三(C6-C30)芳基甲硅烷基;二(C1-C30)烷基(C6-C30)芳基甲硅烷基;(C1-C30)烷基二(C6-C30)芳基甲硅烷基;氨基;单-或二-(C1-C30)烷基氨基;单-或二-(C6-C30)芳基氨基;(C1-C30)烷基(C6-C30)芳基氨基;(C1-C30)烷基羰基;(C1-C30)烷氧基羰基;(C6-C30)芳基羰基;二(C6-C30)芳基硼羰基;二(C1-C30)烷基硼羰基;(C1-C30)烷基(C6-C30)芳基硼羰基;(C6-C30)芳基(C1-C30)烷基;以及(C1-C30)烷基(C6-C30)芳基。根据本公开的一个实施例,所述取代基各自独立地是选自由以下组成的组的至少一个:氘、(C1-C6)烷基、未取代的或被一个或多个氘取代的(C6-C12)芳基、和(5元至15元)杂芳基。特别地,所述取代基各自独立地可以是选自由以下组成的组的至少一个:氘、甲基、叔丁基、苯基、萘基、被一个或多个氘取代的苯基、和咔唑基。
由式1表示的化合物可以由下式1-1或1-2表示:
其中
R1至R6、Ar1和a至f如式1中所定义,前提是在式1-1中d是1或2并且在式1-2中b是1、2或3。
在式1中,Ar1表示取代或未取代的(C6-C30)芳基、或取代或未取代的(5元至30元)杂芳基。根据本公开的一个实施例,Ar1是取代或未取代的(C6-C24)芳基或取代或未取代的(5元至20元)杂芳基。根据本公开的另一个实施例,Ar1是未取代的或被选自以下的一个或多个取代的(C6-C24)芳基:氘、一个或多个(C1-C6)烷基、一个或多个(C6-C12)芳基、一个或多个被氘取代的(C6-C12)芳基和一个或多个(5元至15元)杂芳基;或未取代的或被选自以下的一个或多个取代的(5元至20元)杂芳基:氘、一个或多个(C6-C12)芳基和一个或多个被氘取代的(C6-C12)芳基。例如,Ar1可以是苯基、萘基、联苯基、菲基、三联苯基、三亚苯基、萘基苯基、苯基萘基、苯基菲基、二苯基芴基、二苯基苯并芴基、被一个或多个氘取代的苯基、被一个或多个氘取代的联苯基、被一个或多个氘取代的萘基、被一个或多个氘取代的苯基萘基、被叔丁基取代的苯基、二甲基芴基、二甲基苯并芴基、被咔唑基取代的苯基、二苯并呋喃基、二苯并噻吩基、苯并萘并呋喃基、苯并萘并噻吩基、被一个或多个氘取代的二苯并呋喃基、被苯基取代的苯并呋喃基、被苯基取代的苯并噻吩基、被苯基取代的苯并噁唑基、被苯基取代的咔唑基、被苯基取代的萘并噁唑基、被一个或多个氘取代的苯基萘并噁唑基等。
在式1中,Ar2在位置R1至R4之一处连接至(*表示与Ar2连接的位置)。不与连接的R1至R4以及R5和R6各自独立地表示氢、氘、卤素、氰基、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的(5元至30元)杂芳基。根据本公开的一个实施例,不与连接的R1至R4各自独立地是氢、氘、或取代或未取代的(C6-C12)芳基,并且R5和R6各自独立地是氢或氘。根据本公开的另一个实施例,不与连接的R1至R4各自独立地是氢、氘、或未取代的(C6-C12)芳基,并且R5和R6各自独立地是氢或氘。例如,不与连接的R1至R4可以各自独立地是氢、氘、苯基等。
根据本公开的一个实施例,在式1中,Ar1是取代或未取代的(C6-C24)芳基、或取代或未取代的(5元至20元)杂芳基;不与连接的R1至R4各自独立地是氢、氘、或取代或未取代的(C6-C12)芳基;并且R5和R6各自独立地是氢或氘。
根据本公开的另一个实施例,在式1中,Ar1是未取代的或被选自以下的一个或多个取代的(C6-C24)芳基:氘、一个或多个(C1-C6)烷基、一个或多个(C6-C12)芳基、一个或多个被氘取代的(C6-C12)芳基和一个或多个(5元至15元)杂芳基;或未取代的或被选自以下的一个或多个取代的(5元至20元)杂芳基:氘、一个或多个(C6-C12)芳基和一个或多个被氘取代的(C6-C12)芳基;不与连接的R1至R4各自独立地是氢、氘、或未取代的(C6-C12)芳基;并且R5和R6各自独立地是氢或氘。
在本公开的式中,如果相邻取代基彼此连接以形成环,则所述环可以是取代或未取代的单环或多环(3元至30元)脂环族环或芳香族环、或其组合,其中所形成的环可以含有至少一个选自B、N、O、S、Si和P,优选N、O和S的杂原子。根据本公开的一个实施例,环骨架原子的数目可以是5至20。根据本公开的另一个实施例,环骨架原子的数目可以是5至15。例如,稠环可以是取代或未取代的二苯并噻吩环、取代或未取代的二苯并呋喃环、取代或未取代的萘环、取代或未取代的菲环、取代或未取代的芴环、取代或未取代的苯并噻吩环、取代或未取代的苯并呋喃环、取代或未取代的吲哚环、取代或未取代的茚环、取代或未取代的苯环、或取代或未取代的咔唑环。
在本公开的式中,(亚)杂芳基各自独立地可以含有至少一个选自B、N、O、S、Si和P的杂原子。此外,杂原子可以与选自由以下组成的组的至少一个取代基键合:氢、氘、卤素、氰基、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(5元至30元)杂芳基、取代或未取代的(C3-C30)环烷基、取代或未取代的(C1-C30)烷氧基、取代或未取代的三(C1-C30)烷基甲硅烷基、取代或未取代的二(C1-C30)烷基(C6-C30)芳基甲硅烷基、取代或未取代的(C1-C30)烷基二(C6-C30)芳基甲硅烷基、取代或未取代的三(C6-C30)芳基甲硅烷基、取代或未取代的单-或二-(C1-C30)烷基氨基、取代或未取代的单-或二-(C6-C30)芳基氨基、以及取代或未取代的(C1-C30)烷基(C6-C30)芳基氨基。
由式1表示的化合物包括以下化合物,但不限于此。
在式中,Dn意指式1中的n个氢被氘替代。例如,在化合物C-65中,其意指键合至所述化合物的碳原子的1至26个氢原子被氘取代。
根据本公开的具有式1的化合物可以通过本领域技术人员已知的合成方法以及例如如以下反应方案1和2所示制备,但不限于此。
[反应方案1]
[反应方案2]
在反应方案1和2中,Ar1、R1至R6以及a至f如式1中所定义,并且Hal表示卤素。
此外,由式1表示的化合物的非氘化衍生物可以通过已知的偶联或取代反应制备。所述氘化衍生物可以通过类似的方法使用氘化前体材料,或更一般地,在路易斯酸如三氯化铝或乙基氯化铝、H/D交换催化剂如三氟甲磺酸或三氟甲磺酸-D等的存在下用D6-苯处理非氘化化合物来制备。此外,氘化度可以通过改变反应条件如反应温度来控制。
尽管以上描述了由式1表示的化合物的说明性合成实例,但是本领域技术人员将能够容易地理解它们全部基于布赫瓦尔德-哈特维希(Buchwald-Hartwig)交叉偶联反应、N-芳基化反应、酸化蒙脱土(H-mont)介导的醚化反应、宫浦(Miyaura)硼基化反应、铃木(Suzuki)交叉偶联反应、分子内酸诱导的环化反应、Pd(II)催化的氧化环化反应、格氏反应(Grignard reaction)、赫克反应(Heck reaction)、脱水环合反应、SN1取代反应、SN2取代反应、膦介导的还原环化反应等,并且即使键合了上述式1中所定义但在具体的合成实例中未指定的取代基,上述反应也进行。
本公开提供了一种包含由式1表示的有机电致发光化合物的有机电致发光材料,以及一种包含所述有机电致发光材料的有机电致发光装置。所述材料可以仅由根据本公开的有机电致发光化合物组成,或者可以进一步包含有机电致发光材料中包括的常规材料。
根据本公开的有机电致发光装置包括第一电极、第二电极、和在第一电极与第二电极之间的至少一个有机层,其中所述有机层可以包含至少一种由式1表示的有机电致发光化合物。
第一电极和第二电极之一可以是阳极,并且另一个可以是阴极。有机层可以包含发光层,并且可以进一步包含选自空穴注入层、空穴传输层、空穴辅助层、发光辅助层、电子传输层、电子缓冲层、电子注入层、中间层、空穴阻挡层、以及电子阻挡层的至少一个层。
第二电极可以是半透反射式电极或反射电极,并且根据形成的材料的种类,有机电致发光装置可以是顶部发光型、底部发光型、或两侧发光型。
第一电极和第二电极可以各自由透射式导电材料、半透反射式导电材料、或反射式导电材料形成。根据形成第一电极和第二电极的材料的种类,有机电致发光装置可以是顶部发光型、底部发光型、或两侧发光型。此外,空穴注入层可以进一步掺杂有p型掺杂剂,并且电子注入层可以进一步掺杂有n型掺杂剂。
本公开的由式1表示的有机电致发光化合物可以包含在发光层、空穴注入层、空穴传输层、空穴辅助层、发光辅助层、电子传输层、电子缓冲层、电子注入层、中间层、空穴阻挡层、以及电子阻挡层中的至少一个中,优选地,可以包含在发光层中。当在发光层中使用时,本公开的由式1表示的有机电致发光化合物可以作为主体材料被包含。优选地,发光层可以进一步包含至少一种掺杂剂。如果需要,本公开的有机电致发光化合物可以用作共主体材料。也就是说,发光层可以进一步包含除了本公开的由式1表示的有机电致发光化合物(第一主体材料)之外的化合物作为第二主体材料。第一主体材料与第二主体材料之间的重量比是1:99至99:1。
包含在本公开的有机电致发光装置中的掺杂剂是至少一种磷光掺杂剂或荧光掺杂剂,优选地是至少一种荧光掺杂剂。应用于本公开的有机电致发光装置的荧光掺杂剂材料不受特别限制。
作为包含在本公开的有机电致发光装置中的掺杂剂,例如,可以举例说明由式40表示的缩合的多环胺衍生物,但不限于此。
其中
Ar41表示取代或未取代的(C6-C50)芳基或苯乙烯基;La表示单键、取代或未取代的(C6-C30)亚芳基、或取代或未取代的(3元至30元)杂亚芳基;Ar42和Ar43各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的(3元至30元)杂芳基,或者可以与一个或多个相邻取代基连接以形成(3元至30元)单环或多环的脂环族环、芳香族环、或其组合,其中所形成的脂环族环、芳香族环或其组合的碳原子可以被一个或多个选自N、O和S的杂原子替代;jj是1或2,并且如果jj是2,则每个可以相同或不同。
有机层可以进一步包含至少一种选自由基于芳基胺的化合物和基于苯乙烯基芳基胺的化合物组成的组的化合物。
此外,在本公开的有机电致发光装置中,有机层可以进一步包含选自由以下组成的组的至少一种金属:周期表的第1族的金属、第2族的金属、第4周期的过渡金属、第5周期的过渡金属、镧系元素和d-过渡元素的有机金属、或至少一种包含所述金属的络合化合物。
除了本公开的有机电致发光化合物之外,本公开的有机电致发光装置可以通过进一步包括至少一个含有本领域已知的发射蓝光、红光或绿光的化合物的发光层来发射白光。此外,如果需要,它可以进一步包括发射黄光或橙光的层。
在本公开的有机电致发光装置中,可以优选将选自硫属化物层、金属卤化物层和金属氧化物层中的至少一个层(下文中,“表面层”)放置在一个或两个电极的一个或多个内表面上。具体地,优选将硅或铝的硫属化物(包括氧化物)层放置在电致发光介质层的阳极表面上,并且优选将金属卤化物层或金属氧化物层放置在电致发光介质层的阴极表面上。表面层可以为有机电致发光装置提供运行稳定性。优选地,硫属化物包括SiOX(1≤X≤2)、AlOX(1≤X≤1.5)、SiON、SiAlON等;金属卤化物包括LiF、MgF2、CaF2、稀土金属氟化物等;并且金属氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。
在阳极与发光层之间可以使用空穴注入层、空穴传输层、或电子阻挡层、或其组合。空穴注入层可以是多层以便降低从阳极到空穴传输层或电子阻挡层的空穴注入势垒(或空穴注入电压),其中多层中的每个可以同时使用两种化合物。空穴传输层或电子阻挡层也可以是多层。
在发光层与阴极之间可以使用电子缓冲层、空穴阻挡层、电子传输层、或电子注入层、或其组合。电子缓冲层可以是多层以控制电子的注入并改善发光层与电子注入层之间的界面特性,其中多层中的每个可以同时使用两种化合物。空穴阻挡层或电子传输层也可以是多层,其中多层中的每个可以使用多种化合物。
可以将发光辅助层放置在阳极与发光层之间,或放置在阴极与发光层之间。当将发光辅助层放置在阳极与发光层之间时,它可以用于促进空穴注入和/或空穴传输,或用于防止电子溢出。当将发光辅助层放置在阴极与发光层之间时,它可以用于促进电子注入和/或电子传输,或用于防止空穴溢出。此外,可以将空穴辅助层放置在空穴传输层(或空穴注入层)与发光层之间,并且可以有效促进或阻挡空穴传输速率(或空穴注入速率),从而使得能够控制电荷平衡。此外,可以将电子阻挡层放置在空穴传输层(或空穴注入层)与发光层之间,并且可以阻挡来自发光层的溢出电子并将激子限制在发光层中以防止漏光。当有机电致发光装置包括两个或更多个空穴传输层时,进一步包括的空穴传输层可以用作空穴辅助层或电子阻挡层。空穴辅助层和电子阻挡层可以具有提高有机电致发光装置的效率和/或寿命的作用。
在本公开的有机电致发光装置中,优选将电子传输化合物和还原性掺杂剂的混合区域、或空穴传输化合物和氧化性掺杂剂的混合区域放置在一对电极的至少一个表面上。在这种情况下,电子传输化合物被还原成阴离子,并且因此从混合区域向电致发光介质注入并且传输电子变得更容易。此外,空穴传输化合物被氧化成阳离子,并且因此从混合区域向电致发光介质注入并且传输空穴变得更容易。优选地,氧化性掺杂剂包括各种路易斯酸和受体化合物;并且还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属、及其混合物。还原性掺杂剂层可以用作电荷产生层,以制备具有两个或更多个发射白光的发光层的有机电致发光装置。
根据本公开的一个实施例,有机电致发光材料可以被用作用于白色有机发光装置的发光材料。根据R(红色)、G(绿色)、B(蓝色)、或YG(黄绿色)发光单元的布置,已经提出了以各种结构的白色有机发光装置,如平行并排布置方法、堆叠布置方法、或CCM(颜色转换材料)方法等。此外,根据本公开的一个实施例,有机电致发光材料还可以应用于包含QD(量子点)的有机电致发光装置。
为了形成本公开的有机电致发光装置的每个层,可以使用干法成膜方法如真空蒸发、溅射、等离子体、离子镀等,或湿法成膜方法如旋涂、喷墨印刷、浸涂、流涂等。
当使用湿法成膜方法时,可以通过将形成每个层的材料溶解或扩散到任何合适溶剂如乙醇、氯仿、四氢呋喃、二噁烷等中来形成薄膜。对溶剂没有特别限制,只要形成每个层的材料在溶剂中是可溶的或可分散的,这在形成膜时不会引起任何问题。
可以通过使用本公开的有机电致发光装置来生产显示***,例如用于智能手机、平板电脑、笔记本电脑、PC、TV或汽车的显示***;或照明***,例如室外或室内照明***。
在下文中,将参考本公开的代表性化合物详细说明本公开的化合物的制备方法、及所述化合物的特性、以及包含所述化合物的有机电致发光装置的发光特性。然而,本公开不受限于以下实例。
实例1:化合物C-1的制备
将化合物A-1(10.5g,0.029mol)、化合物A-2(8.9g,0.032mol)、Pd(OAc)2(0.33g,0.001mol)、s-phos(1.2g,0.002mmol)、K2CO3(12.1g,0.088mol)、26mL的乙腈、52mL的蒸馏水和126mL的甲苯添加到烧瓶中并且在120℃下搅拌16小时。将混合物冷却至室温、用乙酸乙酯(EA)萃取,并且将有机层用蒸馏水洗涤。将获得的有机层减压蒸馏并通过柱色谱法分离以获得化合物C-1(4g,26.5%)。
MW | 熔点 | |
C-1 | 530.20 | 394℃ |
实例2:化合物C-35的制备
1)化合物B-3的制备
将化合物9-溴蒽(20g,0.077mol)、化合物B-4(25.1g,0.085mol)、Pd(PPh3)4(4.5g,0.003mol)、K2CO3(32g,0.23mol)、97mL的乙醇、97mL的蒸馏水和390mL的甲苯添加到烧瓶中并在100℃下搅拌。在12小时后,将混合物冷却至室温、用二氯甲烷萃取,并且将有机层用蒸馏水洗涤。将获得的有机层减压蒸馏并通过柱色谱法分离以获得化合物B-3(25.8g,96.6%)。
2)化合物B-2的制备
将化合物B-3(25.8g,0.074mol)添加到烧瓶中、溶解在374mL的二甲基甲酰胺(DMF)中,并且向其中添加N-溴代琥珀酰亚胺(13.3g,0.074mol)。将混合物在室温下搅拌18小时、用二氯甲烷萃取,并且将有机层用蒸馏水洗涤。将获得的有机层减压蒸馏并通过柱色谱法分离以获得化合物B-2(30g,94.6%)。
3)化合物B-1的制备
将化合物B-2(30g,0.070mol)添加到烧瓶中,并且向其中添加700mL的四氢呋喃。在-78℃下缓慢添加N-BuLi(37mL,2.5M,0.092mol)。在10分钟后,向其中添加硼酸三甲酯(10.3mL,0.092mol)。在将混合物搅拌12小时后,向其中添加蒸馏水。将有机层用乙酸乙酯萃取,并且使用硫酸镁除去剩余水分。将有机层减压蒸馏,并且通过添加己烷凝固以获得化合物B-1(16g,58.8%)。
4)化合物C-35的制备
将化合物A-1(6g,0.016mol)、化合物B-1(8.4g,0.021mol)、Pd(PPh3)4(0.97g,0.00084mol)、K2CO3(6.9g,0.050mol)、20mL的乙醇、20mL的蒸馏水和84mL的甲苯添加到烧瓶中并将混合物在130℃下搅拌。在16小时后,将混合物冷却至室温、用乙酸乙酯萃取,并且将有机层用蒸馏水洗涤。将获得的有机层减压蒸馏并通过柱色谱法分离以获得化合物C-35(5.5g,52.7%)。
MW | 熔点 | |
C-35 | 620.75 | 347℃ |
装置实例1:生产包含根据本公开的化合物的OLED
如下生产使用根据本公开的有机电致发光化合物的OLED:将用于OLED的玻璃基板上的透明电极铟锡氧化物(ITO)薄膜(10Ω/sq)(日本吉奥马有限公司(GEOMATEC CO.,LTD.,Japan))用丙酮、乙醇和蒸馏水依次进行超声洗涤,并且然后储存在异丙醇中。将ITO基板安装在真空气相沉积设备的基板支架上。将化合物HI-1引入真空气相沉积设备的小室中,并且然后将设备的腔室中的压力控制到10-6托。此后,向小室施加电流以使以上引入的材料蒸发,从而在ITO基板上形成具有60nm厚度的第一空穴注入层。接下来,将化合物HI-2引入真空气相沉积设备的另一个小室中,并通过向小室施加电流使所述化合物蒸发,从而在第一空穴注入层上形成具有5nm厚度的第二空穴注入层。然后将化合物HT-1引入真空气相沉积设备的另一个小室中,并通过向小室施加电流使所述化合物蒸发,从而在第二空穴注入层上形成具有20nm厚度的第一空穴传输层。然后将化合物HT-2引入真空气相沉积设备的另一个小室中,并通过向小室施加电流使所述化合物蒸发,从而在第一空穴传输层上形成具有5nm厚度的第二空穴传输层。在形成空穴注入层和空穴传输层之后,如下在其上形成发光层:将化合物C-1引入真空气相沉积设备的一个小室中作为发光层的主体,并将化合物BD引入另一个小室中。将两种材料以不同的速率蒸发并以基于主体和掺杂剂的总量的2wt%的掺杂量沉积掺杂剂以在第二空穴传输层上形成具有20nm厚度的发光层。接下来,在另外两个小室中以1:1的速率分别以50重量%的量蒸发化合物ET-1和化合物EI-1,以在发光层上沉积具有35nm厚度的电子传输层。在电子传输层上将化合物EI-1沉积为具有2nm厚度的电子注入层之后,通过另一个真空气相沉积设备在电子注入层上沉积具有80nm厚度的Al阴极。由此,生产了OLED。
装置实例2:生产包含根据本公开的化合物的OLED
除了使用化合物C-35替代化合物C-1作为发光层的主体材料之外,以与装置实例1中相同的方式生产OLED。
对比实例:生产包含常规化合物的OLED
除了使用化合物BH-1替代化合物C-1作为发光层的主体材料之外,以与装置实例1中相同的方式生产OLED。
结果是,装置实例1和2以及对比实例的有机电致发光装置的基于1,000尼特亮度的驱动电压、电流效率和电致发光波长的测量结果在下表1中示出。
[表1]
从上表1中可以看出,当与使用对比化合物的装置相比时,包含根据本公开的有机电致发光化合物作为主体材料的有机电致发光装置展现出更低的驱动电压,并且显著改善了电流效率特征。
在装置实例和对比实例中使用的化合物在下表2中示出。
[表2]
Claims (9)
1.一种有机电致发光化合物,其由下式1表示:
其中
Ar1表示取代或未取代的(C6-C30)芳基、或取代或未取代的(5元至30元)杂芳基;
R5和R6各自独立地表示氢、氘、卤素、氰基、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的(5元至30元)杂芳基;
其中Ar2在位置R1至R4之一处连接至(*表示与Ar2连接的位置),并且不与连接的R1至R4各自独立地表示氢、氘、卤素、氰基、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的(5元至30元)杂芳基;
a和d各自独立地表示1至3的整数,并且b、c、e和f各自独立地表示1至4的整数;
其中如果a至f是2或更大的整数,则每个R1至每个R6可以彼此相同或不同。
3.根据权利要求1所述的有机电致发光化合物,其中,在R1至R6和Ar1中,取代的烷基、取代的芳基和取代的杂芳基的取代基各自独立地是选自由以下组成的组的至少一个:氘;卤素;氰基;羧基;硝基;羟基;(C1-C30)烷基;卤代(C1-C30)烷基;(C2-C30)烯基;(C2-C30)炔基;(C1-C30)烷氧基;(C1-C30)烷硫基;(C3-C30)环烷基;(C3-C30)环烯基;(3元至7元)杂环烷基;(C6-C30)芳氧基;(C6-C30)芳硫基;未取代的或被一个或多个(C6-C30)芳基取代的(3元至30元)杂芳基;未取代的或被氘、一个或多个(C1-C30)烷基和一个或多个(3元至30元)杂芳基中的至少一个取代的(C6-C30)芳基;三(C1-C30)烷基甲硅烷基;三(C6-C30)芳基甲硅烷基;二(C1-C30)烷基(C6-C30)芳基甲硅烷基;(C1-C30)烷基二(C6-C30)芳基甲硅烷基;氨基;单-或二-(C1-C30)烷基氨基;单-或二-(C6-C30)芳基氨基;(C1-C30)烷基(C6-C30)芳基氨基;(C1-C30)烷基羰基;(C1-C30)烷氧基羰基;(C6-C30)芳基羰基;二(C6-C30)芳基硼羰基;二(C1-C30)烷基硼羰基;(C1-C30)烷基(C6-C30)芳基硼羰基;(C6-C30)芳基(C1-C30)烷基;以及(C1-C30)烷基(C6-C30)芳基。
7.一种有机电致发光材料,其包含根据权利要求1所述的有机电致发光化合物。
8.一种有机电致发光装置,其包含根据权利要求1所述的有机电致发光化合物。
9.根据权利要求8所述的有机电致发光装置,其中,所述有机电致发光化合物包含在发光层中。
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