CN112135816B - 新的化合物和包含其的有机发光器件 - Google Patents
新的化合物和包含其的有机发光器件 Download PDFInfo
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- CN112135816B CN112135816B CN201980033194.6A CN201980033194A CN112135816B CN 112135816 B CN112135816 B CN 112135816B CN 201980033194 A CN201980033194 A CN 201980033194A CN 112135816 B CN112135816 B CN 112135816B
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- 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
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 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
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
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Abstract
提供了新的化合物和使用其的有机发光器件。
Description
技术领域
相关申请的交叉引用
本申请要求于2018年10月16日向韩国知识产权局提交的韩国专利申请第10-2018-0123388号的权益,其公开内容在此通过引用整体并入。
本公开内容涉及新的化合物和使用其的有机发光器件。
背景技术
通常,有机发光是指其中使用有机材料将电能转化成光能的现象。利用有机发光现象的有机发光器件具有宽视角、优异的对比度、快速的响应时间,以及优异的亮度、驱动电压和响应速度特性,并因此正在进行许多研究。
有机发光器件通常具有包括阳极、阴极、以及在阳极与阴极之间的有机材料层的结构。有机材料层经常由包含不同材料的多层构成以提高有机发光器件的效率和稳定性,例如,有机材料层可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等构成。在这样的有机发光器件的结构中,如果在两个电极之间施加电压,则空穴从阳极注入到有机材料层中并且电子从阴极注入到有机材料层中,并且当注入的空穴和电子相遇时,形成激子,并且当激子落回至基态时发光。
持续需要开发用于在有机发光器件中使用的有机材料的新材料。
[现有技术文献]
[专利文献]
(专利文献0001)韩国特许专利公开第10-2000-0051826号。
发明内容
技术问题
本公开内容涉及新的化合物和使用其的有机发光器件。
技术方案
提供了由以下化学式1表示的化合物:
[化学式1]
在化学式1中,
R为Si(R1)(R2)(R3),
R1至R3各自独立地为氢;氘;经取代或未经取代的C1-60烷基;或经取代或未经取代的C6-60芳基;(三(C1-60烷基)甲硅烷基)-(C1-10亚烷基)-;或(三(C6-60芳基)甲硅烷基)-(C1-10亚烷基)-,或者R1和R2连接以形成环,条件是R1至R3不都是经取代或未经取代的C1-60烷基,
L1为单键;亚苯基;或者萘二基,
m和n各自独立地为0至3的整数,
R4和R5各自独立地为氢;氘;卤素;氰基;经取代或未经取代的C1-60烷基;经取代或未经取代的C1-60烷氧基;经取代或未经取代的C1-60硫代烷基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C5-60杂芳基,
Ar3为氘;C1-10烷基;经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C5-60杂芳基,
Ar1和Ar2各自独立地为氢;氘;经取代或未经取代的C1-60烷基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C5-60杂芳基,或者彼此连接以形成C3-60环烷基或由以下化学式2表示的取代基,
[化学式2]
在化学式2中,p和q各自独立地为0至4的整数,
R6和R7各自独立地为氢;氘;卤素;氰基;经取代或未经取代的C1-60烷基;经取代或未经取代的C1-60烷氧基;经取代或未经取代的C1-60硫代烷基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C5-60杂芳基。
还提供了有机发光器件,其包括:第一电极;与第一电极相对的第二电极;以及在第一电极与第二电极之间的一个或更多个有机材料层,其中一个或更多个有机材料层包含由化学式1表示的化合物。
有益效果
由化学式1表示的化合物可以用作有机发光器件的有机材料层的材料,并且在有机发光器件中改善效率,实现低驱动电压和/或寿命特性。此外,由化学式1表示的化合物可以用作用于空穴注入、空穴传输、空穴注入和传输、发光、电子传输或电子注入的材料。
附图说明
图1示出了由基底1、阳极2、发光层3和阴极4构成的有机发光器件的实例。
图2示出了由基底1、阳极2、空穴注入层5、空穴传输层6、发光层7、电子传输层8和阴极4构成的有机发光器件的实例。
具体实施方式
在下文中,将更详细地说明本公开内容。
提供了由以上化学式1表示的化合物。
如本文中所使用的,或/>意指与另外的取代基连接的键。
如本文中所使用的,术语“经取代或未经取代的”意指未经取代或经选自以下的一个或更多个取代基取代:氘;卤素;腈基;硝基;羟基;羰基;酯基;酰亚胺基;氨基;氧化膦基;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;或包含N、O和S原子中的一者或更多者的杂环基,或者未经取代或经以上描述的取代基中的两个或更多个相连接的取代基取代。例如,“两个或更多个取代基相连接的取代基”可以为联苯基。即,联苯基可以为芳基,或者其可以解释为两个苯基相连接的取代基。
在整个说明书中,羰基的碳数没有特别限制,但优选为1至40。具体地,羰基可以为以下结构的化合物,但不限于此。
在整个说明书中,酯基的氧可以经线性、支化或环状的C1-25烷基或C6-25芳基取代。具体地,酯基可以为以下结构的化合物,但不限于此。
在整个说明书中,酰亚胺基的碳数没有特别限制,但优选为1至25。具体地,酰亚胺基可以为以下结构的化合物,但不限于此。
在整个说明书中,甲硅烷基可以具体地为三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但不限于此。
在整个说明书中,硼基可以具体地为三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、苯基硼基等,但不限于此。
在整个说明书中,卤素基团的实例可以包括氟、氯、溴、或碘。
在整个说明书中,烷基可以为线性或支化的,并且碳数没有特别限制,但优选为1至40。根据一个实施方案,烷基的碳数为1至20。根据一个实施方案,烷基的碳数为1至10。根据一个实施方案,烷基的碳数为1至6。烷基的具体实例可以包括甲基、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、环庚基甲基、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-甲基己基等,但不限于此。
在整个说明书中,烯基可以为线性或支化的,并且碳数没有特别限制,但优选为2至40。根据一个实施方案,烯基的碳数为2至20。根据另一个实施方案,烯基的碳数为2至10。根据又一个实施方案,烯基的碳数为2至6。具体实例可以包括乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-双(二苯基-1-基)乙烯基-1-基、茋基、苯乙烯基等,但不限于此。
在整个说明书中,环烷基没有特别限制,但碳数优选为3至60,并且根据一个实施方案,环烷基的碳数为3至30。根据另一个实施方案,环烷基的碳数为3至20。根据又一个实施方案,环烷基的碳数为3至6。具体实例可以包括环丙基、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,但不限于此。
在整个说明书中,芳基没有特别限制,但优选具有6至60的碳数,并且其可以为单环芳基或多环芳基。根据一个实施方案,芳基的碳数为6至30。根据一个实施方案,芳基的碳数为6至20。作为单环芳基,可以提及苯基、联苯基、三联苯基等,但不限于此。作为多环芳基,可以提及萘基、蒽基、菲基、芘基、苝基、基、芴基等,但不限于此。
在整个说明书中,芴基可以为经取代的,并且两个取代基可以连接以形成螺环结构。在芴基被取代的情况下,芴基可以为等,但不限于此。
在整个说明书中,杂环基为包含选自O、N、P、Si和S中的一者或更多者作为杂原子的杂环基,并且碳数没有特别限制,但优选为2至60。作为杂环基的实例,可以提及噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、/>二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并/>唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基、异/>唑基、噻二唑基、吩噻嗪基和二苯并呋喃基等,但不限于此。
在整个说明书中,芳烷基、芳烯基、烷基芳基和芳基胺基中的芳基如芳基中所说明的。在整个说明书中,芳烷基、烷基芳基和烷基胺基中的烷基如烷基中所说明的。在整个说明书中,对于杂芳基胺中的杂芳基,可以应用关于杂环基的说明。在整个说明书中,芳烯基中的烯基如烯基中所说明的。在整个说明书中,对于亚芳基,除了为二价以外,可以应用关于芳基的说明。在整个说明书中,对于亚杂芳基,除了为二价以外,可以应用关于杂环基的说明。在整个说明书中,对于烃环,可以应用关于芳基或环烷基的说明,不同之处在于烃环不是一价的并且是通过两个取代基的键合而形成的。在整个说明书中,对于杂环,可以应用关于杂环基的说明,不同之处在于杂环不是一价基团并且是通过两个取代基的键合而形成的。
优选地,化学式1可以为以下化学式1-1至1-5中的任一者。
[化学式1-1]
[化学式1-2]
[化学式1-3]
[化学式1-4]
[化学式1-5]
在化学式1-1至1-5中,
R8和R9各自独立地为氢;或者经取代或未经取代的C1-60烷基,以及
m、n、p、q、R、R4至R7、L1和Ar3如上所限定。
优选地,R1至R3各自独立地为甲基;异丙基;叔丁基;苯基;或三甲基甲硅烷基-亚乙基。
优选地,R1至R3中的至少一者可以为苯基。
优选地,L1可以为单键;或者亚苯基。
此外,优选地,m和n二者均可以为0。
优选地,p和q可以各自独立地为0或1。
优选地,R6和R7可以各自独立地为氢;或者C1-10烷基,更优选地,氢、甲基或叔丁基。
优选地,R8和R9可以各自独立地为氢;或者C1-10烷基,更优选地,氢、甲基或叔丁基。
优选地,Ar3可以为氘;C1-10烷基;或者未经取代或经三(C1-5烷基)甲硅烷基取代的苯基;或萘基。
例如,由化学式1表示的化合物可以为选自以下化合物中的一者:
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同时,由化学式1表示的化合物可以通过如以下反应式1所示的制备方法来制备:
[反应式1]
反应式1为Suzuki偶联反应,优选每个反应在钯催化剂和碱的存在下进行,并且用于Suzuki偶联反应的反应器可以根据本领域的知识进行改进。将在下面的制备例中详细地说明制备方法。
此外,提供了包含由以上化学式1表示的化合物的有机发光器件。例如,提供了有机发光器件,其包括:第一电极;与第一电极相对的第二电极;以及在第一电极与第二电极之间的一个或更多个有机材料层,其中一个或更多个有机材料层包含由化学式1表示的化合物。包含由化学式1表示的化合物的有机材料层为发光层。
由化学式1表示的化合物通过引入硅烷基的庞大结构而具有改善的溶解度,并因此具有提高的溶液可加工性。因此,包含由化学式1表示的化合物的有机发光器件可以具有改善的效率和寿命。
此外,当引入硅烷基时,材料的玻璃化转变温度提高,并因此提高了材料的稳定性,并且在制造膜时,也提高膜的稳定性。因此,可以预期包含由化学式1表示的化合物的有机发光器件具有高效率和长寿命。
本公开内容的有机发光器件的有机材料层可以具有单层结构,但是其可以具有其中堆叠有两个或更多个有机材料层的多层结构。例如,本公开内容的有机发光器件可以具有包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等作为有机材料层的结构。然而,有机发光器件的结构不限于此,并且其可以具有更少数量的有机材料层。
此外,有机材料层可以包括空穴注入层、空穴传输层、或者同时执行用于空穴注入和传输的功能的层,并且空穴注入层、空穴传输层、或者同时执行用于空穴注入和传输的功能的层可以包含由化学式1表示的化合物。
此外,有机材料层可以包括发光层,并且发光层可以包含由化学式1表示的化合物。其中,由化学式1表示的化合物可以在发光层中用作掺杂剂,并且更具体地,由化学式1表示的化合物可以在蓝色有机发光器件的发光层中用作掺杂剂。
此外,有机材料层可以包括电子传输层或电子注入层,并且电子传输层或电子注入层可以包含由化学式1表示的化合物。
此外,电子传输层、电子注入层或同时起用于电子传输或电子注入作用的层可以包含由化学式1表示的化合物。
此外,有机材料层可以包括发光层和电子传输层,并且电子传输层可以包含由化学式1表示的化合物。
此外,优选地,发光层还可以包含由以下化学式3表示的化合物。
[化学式3]
在化学式3中,
L2为单键;或者经取代或未经取代的C6-60亚芳基,
Ar4和Ar5各自独立地为经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C5-60杂芳基。
其中,由化学式3表示的化合物可以在发光层中用作主体材料,并且更具体地,由化学式3表示的化合物可以在蓝色有机发光器件的发光层中用作主体。
优选地,L2可以为单键;或亚苯基。
优选地,Ar4和Ar5可以各自独立地为选自以下中的一者:
例如,由化学式3表示的化合物可以为选自以下化合物中的一者:
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根据本公开内容的有机发光器件可以为其中阳极、一个或更多个有机材料层和阴极顺序地堆叠在基底上的正常型有机发光器件。此外,根据本公开内容的有机发光器件可以为其中阴极、一个或更多个有机材料层和阳极顺序地堆叠在基底上的倒置型有机发光器件。例如,根据本公开内容的一个实施方案的有机发光器件的结构示于图1和图2中。
图1示出了由基底1、阳极2、发光层3和阴极4构成的有机发光器件的实例。在该结构中,由化学式1表示的化合物可以包含在发光层中。此外,在发光层中,还可以包含由化学式3表示的化合物。
图2示出了由基底1、阳极2、空穴注入层5、空穴传输层6、发光层7、电子传输层8和阴极4构成的有机发光器件的实例。在该结构中,由化学式1表示的化合物可以包含在空穴注入层、空穴传输层、发光层和电子传输层中的一个或更多个层中。
根据本公开内容的有机发光器件可以使用本领域已知的材料和方法来制备,不同之处在于一个或更多个有机材料层包含由化学式1表示的化合物。此外,在有机发光器件包括复数个有机材料层的情况下,有机材料层可以由相同或不同的材料形成。
例如,根据本公开内容的有机发光器件可以通过顺序地堆叠第一电极、有机材料层和第二电极来制造。其中,使用PVD(物理气相沉积)例如溅射或电子束蒸镀,可以在基底上沉积金属或导电金属氧化物或其合金以形成阳极,并且可以在阳极上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机材料层,然后可以在有机材料层上沉积可以用作阴极的材料。此外,有机发光器件可以通过在基底上顺序地沉积阴极材料、有机材料层和阳极材料来制造。
此外,当制造有机发光器件时,由化学式1表示的化合物可以通过溶液涂覆以及真空沉积形成为有机材料层。特别地,由于由化学式1表示的化合物在用于溶液涂覆的溶剂中具有优异的溶解度,因此容易应用溶液涂覆。其中,溶液涂覆意指旋涂、浸涂、刮涂、喷墨印刷、丝网印刷、喷洒、辊涂等,但不限于此。
因此,提供了包含由化学式1表示的化合物和溶剂的涂覆组合物。
溶剂没有特别限制,只要其可以溶解或分散根据本公开内容的化合物即可,例如,可以提及:含氯的溶剂,例如氯仿、二氯甲烷、1,2-二氯乙烷、1,1,2-三氯乙烷、氯苯、邻二氯苯等;基于醚的溶剂,例如四氢呋喃、二烷等;基于芳族烃的溶剂,例如甲苯、二甲苯、三甲基苯、均三甲苯等;基于脂族烃的溶剂,例如环己烷、甲基环己烷、正戊烷、正己烷、正庚烷、正辛烷、正壬烷、正癸烷等;基于酮的溶剂,例如丙酮、甲基乙基酮、环己酮等;基于酯的溶剂,例如乙酸乙酯、乙酸丁酯、乙基溶纤剂乙酸酯等;多元醇及其衍生物,例如乙二醇、乙二醇单丁醚、乙二醇单乙醚、乙二醇单甲醚、二甲氧基乙烷、丙二醇、二乙氧基甲烷、三乙二醇单乙醚、甘油、1,2-己二醇等;基于醇的溶剂,例如甲醇、乙醇、丙醇、异丙醇、环己醇等;基于亚砜的溶剂,例如甲基亚砜等;基于酰胺的溶剂,例如N-甲基-2-吡咯烷酮、N,N-二甲基甲酰胺等;基于苯甲酸酯的溶剂,例如苯甲酸丁酯、2-甲氧基苯甲酸甲酯等;四氢化萘;3-苯氧基-甲苯等。此外,可以单独使用上述溶剂中的一种或者可以混合并使用其两种或更多种。
此外,涂覆组合物的粘度优选为1cP至10cP,并且在该范围内,其容易涂覆。此外,根据本公开内容的化合物在涂覆组合物中的浓度可以优选为0.1重量/体积%至20重量/体积%。
根据本公开内容,还提供了使用上述涂覆组合物来形成功能层的方法。具体地,该方法包括以下步骤:通过溶液法涂覆上述涂覆组合物;以及对涂覆的涂覆组合物进行热处理。
在热处理步骤中,热处理温度可以优选为150℃至230℃。此外,热处理时间为1分钟至3小时,更优选10分钟至1小时。此外,优选热处理在惰性气体气氛例如氩气、氮气等下进行。
此外,有机发光器件可以通过在基底上顺序地沉积阴极材料、有机材料层和阳极材料来制造(WO 2003/012890)。然而,制造方法不限于此。
例如,第一电极可以为阳极并且第二电极可以为阴极,或者第一电极可以为阴极并且第二电极可以为阳极。
作为阳极材料,优选具有大功函数的材料以促进空穴注入至有机材料层中。阳极材料的具体实例可以包括:金属,例如钒、铬、铜、锌、金、或其合金;金属氧化物,例如氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯、和聚苯胺,但不限于此。
作为阴极材料,优选具有小功函数的材料以促进电子注入至有机材料层中。阴极材料的具体实例可以包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅、或其合金;多层材料,例如LiF/Al或LiO2/Al,但不限于此。
空穴注入层为注入来自电极的空穴的层,并且作为空穴注入材料,可以优选使用这样的化合物:其具有传输空穴的能力,并因此具有从阳极注入空穴的效应和对于发光层或发光材料具有优异的空穴注入效应,防止在发光层中产生的激子移动至电子注入层或电子注入材料,并且具有优异的薄膜形成能力。优选空穴注入材料的HOMO(最高占据分子轨道)在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例可以包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖啶酮的有机材料、基于苝的有机材料、蒽醌、以及基于聚苯胺和聚噻吩的导电聚合物等,但不限于此。
空穴传输层为接收来自空穴注入层的空穴并将空穴传输至发光层的层,并且作为空穴传输材料,优选可以接收来自阳极或空穴注入层的空穴并将其转移至发光层并且具有高空穴迁移率的材料。具体实例可以包括基于芳基胺的有机材料、导电聚合物、和同时包含共轭部分和非共轭部分的嵌段共聚物,但不限于此。
作为发光材料,可以优选使用这样的材料:其可以接收分别来自空穴传输层和电子传输层的空穴和电子并使它们结合,从而发出可见光区域的光,并且对荧光或磷光具有良好的量子效率。具体实例可以包括8-羟基-喹啉铝配合物(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并唑、基于苯并噻唑和基于苯并咪唑的化合物;基于聚(对亚苯基亚乙烯基)(PPV)的聚合物;螺环化合物;聚芴;红荧烯等,但不限于此。
发光层可以包含主体材料和掺杂剂材料。主体材料可以包括稠合芳族环衍生物或含杂环的化合物等。具体地,稠合芳族环衍生物可以包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲衍生物、荧蒽化合物等,含杂环的化合物可以包括咔唑衍生物、二苯并呋喃衍生物、梯子型呋喃化合物、嘧啶衍生物等,但不限于此。
掺杂剂材料可以包括芳族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体地,芳族胺衍生物可以为具有经取代或未经取代的芳基氨基的稠合芳族环衍生物,例如具有芳基氨基的芘、蒽、、二茚并芘等,苯乙烯基胺化合物可以为其中经取代或未经取代的芳基胺经至少一个芳基乙烯基取代的化合物,并且为未经取代的或经选自芳基、甲硅烷基、烷基、环烷基和芳基氨基中的一个或两个或更多个取代基取代的。具体地,可以提及苯乙烯基胺、苯乙烯基二胺、苯乙烯基三胺、苯乙烯基四胺等,但不限于此。此外,金属配合物可以包括铱配合物、铂配合物等,但不限于此。
电子传输层为接收来自电子注入层的电子并将电子传输至发光层的层,并且作为电子传输材料,可以接收来自阴极的电子并将其转移至发光层并且具有高电子迁移率的材料是合适的。其具体实例可以包括:8-羟基喹啉的Al配合物;包含Alq3的配合物;有机自由基化合物;羟基黄酮-金属配合物等,但不限于此。电子传输层可以与如根据现有技术使用的任何期望的阴极材料一起使用。特别地,合适的阴极材料的实例为具有小功函数并且后接铝层或银层的常见材料。具体地,可以提及铈、钡、镱和钐,并且在每种情况下都后接铝层或银层。
电子注入层为注入来自电极的电子的层,并且作为电子注入材料,优选这样的材料:其具有传输电子的能力,具有从阴极注入电子的效应,并且对于发光层或发光材料具有优异的电子注入效应,防止发光层中产生的激子移动至空穴注入层,并且具有优异的形成薄膜的能力。具体地,可以提及芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、/>二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等、及其衍生物、金属配合物化合物和含氮5元环衍生物等,但不限于此。
作为金属配合物化合物,可以提及8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但不限于此。
根据所使用的材料,根据本公开内容的有机发光器件可以为顶部发射型、底部发射型或双发射型。
此外,由化学式1表示的化合物还可以包含在有机太阳能电池或有机晶体管以及有机发光器件中。
将在下面的实施例中详细地说明由化学式1表示的化合物和包含其的有机发光器件的制备。然而,以下实施例仅作为本发明的举例说明提出,并且本发明的范围不受此限制。
制备例1
将化合物A1(11.2g,30mmol)、化合物A2(4.48g,30mmol)、Pd2dba3(1.37g,1.5mmol)、BINAP(2.8g,4.5mmol)和NatBuO(4.32g,45mmol)溶于甲苯(240ml)中,然后,在80℃下搅拌15小时。将反应溶液冷却至室温,引入蒸馏水,在分液漏斗中分离有机层,并用MgSO4除去水分,然后,在减压下除去溶剂。使用二氯甲烷己烷使获得的物质经受柱色谱以分离并纯化化合物A3(9.1g,77%)。MS:[M+H]+=394
制备例2
通过与制备例1相同的方法制备化合物A5,不同之处在于使用化合物A4代替化合物A2。MS:[M+H]+=388
制备例3
将化合物A3(2g,5mmol)、化合物A6(2.85g,7.5mmol)、Pd(PPh3)4(289mg,0.25mmol)和K2CO3(2.07g,15mmol)溶于甲苯(50ml)和蒸馏水(20ml)中,然后,在90℃下搅拌15小时。在分离有机层之后,用MgSO4除去水分,然后,在减压下除去溶剂。使用二氯甲烷己烷使获得的物质经受柱色谱以分离并纯化化合物B1(1.8g,55%)。MS:[M+H]+=650
制备例4
通过与制备例3相同的方法制备化合物B2,不同之处在于使用化合物A5代替化合物A3。MS:[M+H]+=644
实施例1
将化合物C1(1g,2.48mmol)、化合物B1(3.55g,5.47mmol)、Pd2(dba)3(110mg,0.12mmol)、P(tBu)3(73mg,0.36mmol)和NatBuO(0.79g,8.21mmol)溶于甲苯(25ml)中,然后,在100℃下搅拌15小时。将反应溶液冷却至室温,引入蒸馏水,在分液漏斗中分离有机层,并用MgSO4除去水分,然后,在减压下除去溶剂。使用二氯甲烷己烷使获得的物质经受柱色谱以分离并纯化化合物1-1(2.3g,60%)。MS:[M+H]+=1540
实施例2
通过与实施例1相同的方法制备化合物1-2,不同之处在于使用化合物B2代替化合物B1。MS:[M+H]+=1528
实施例3
通过与实施例1相同的方法制备化合物1-3,不同之处在于使用化合物C2代替化合物C1。MS:[M+H]+=1664
实施例4
通过与实施例3相同的方法制备化合物1-4,不同之处在于使用化合物B2代替化合物B1。MS:[M+H]+=1652
制备例5
将化合物A8(2.33g,10mmol)溶于四氢呋喃(100mL)中,并冷却至-78℃。向冷却的反应溶液中滴加2.5M正丁基锂(4.4mL,11mmol)并搅拌1小时。然后,引入化合物A7(3.88g,10mmol)并在室温下搅拌。在反应完成之后,引入碳酸氢钠水溶液以终止反应,然后,用乙酸乙酯和水萃取。将有机层分离,用MgSO4除去水分,然后,在减压下除去溶剂。将获得的物质用乙酸乙酯和己烷重结晶以获得化合物A9。向化合物A9中引入乙酸(50mL)和硫酸(0.05mL),并且将反应溶液在回流下搅拌2小时。在反应完成之后,过滤固体并用水和乙醇洗涤,然后用乙酸乙酯和己烷重结晶以获得化合物C3(2.7g,52%)。
实施例5
通过与实施例1相同的方法制备化合物1-5,不同之处在于使用化合物C3代替化合物C1。MS:[M+H]+=1662
实施例6
通过与实施例5相同的方法制备化合物1-6,不同之处在于使用化合物B2代替化合物B1。MS:[M+H]+=1650
实施例7
将9-溴-10-(萘-1-基)蒽(1.92g,5mmol)、((3-(萘-2-基)苯基)硼酸(1.86g,7.5mmol)、Pd(PPh3)4(0.58g,0.5mmol)和K2CO3(2.07g,15mmol)溶于甲苯(60ml)和蒸馏水(20ml)中,然后,在90℃下搅拌15小时。在将有机层分离之后,用MgSO4除去水分,然后,在减压下除去溶剂。使用二氯甲烷己烷使获得的物质经受柱色谱以分离并纯化化合物2-1。MS:[M+H]+=507
实施例8
通过与实施例7相同的方法制备化合物2-2,不同之处在于使用9-(4-溴苯基)-10-(萘-1-基)蒽(2.3g,5mmol)代替9-溴-10-(萘-1-基)蒽。MS:[M+H]+=583
[实验例1]
将涂覆有厚度为50nm的ITO(氧化铟锡)薄膜的玻璃基底放置在溶解有清洁剂的蒸馏水中,并进行超声清洗。其中,使用来自Fischer Co.的清洁剂,并且使用用过滤器(来自Millipore Co.的产品)过滤两次的蒸馏水。在洗涤ITO 30分钟之后,用蒸馏水进行两次超声清洗10分钟。在用蒸馏水清洗完成之后,用异丙醇、丙酮和甲醇溶剂进行超声清洗,并干燥,然后转移至等离子体清洗机。此外,使用氧等离子体清洗基底5分钟,然后转移至真空沉积设备。
在准备的ITO透明电极上,将导电聚合物和磺酸聚合物的水性分散体以1000rpm旋涂60秒,在80℃下烘烤2分钟,并且在120℃下烘烤15分钟以形成空穴注入层。在空穴注入层上,旋涂三芳基胺聚合物溶液并烘烤以形成空穴传输层。在空穴传输层上,将重量比为95:5的上述化合物2-1和化合物1-1的2重量%甲苯溶液以5000rpm旋涂,在80℃下烘烤2分钟,并且在120℃下烘烤30分钟以形成发光层。将其在氮气气氛下于130℃下干燥10分钟,然后,沉积氟化锂(LiF)至约1nm的膜厚度,并且最后,沉积铝至100nm的薄厚度,从而形成阴极。在该过程中,在将氟化锂的沉积速度保持在将铝的沉积速度保持在/>并将沉积期间的真空度保持在2×10-7托至5×10-6托的同时,制造了有机发光器件。
器件结构:ITO(50nm)/HIL(40nm)/HTL(20nm)/EML(55nm)/LiF(1nm)/Al(100nm)
[实验例2至12]
通过与实验例1相同的方法制造有机发光器件,不同之处在于用于制造发光层的化合物如下表1所示改变。
[比较实验例1至4]
通过与实验例1相同的方法制造有机发光器件,不同之处在于用于制造发光层的化合物如下表1所示改变。
BD1和BD2的结构如下。
对于在实验例1至12和比较实验例1至4中制造的有机发光器件,测量了在10mA/cm2的电流密度下的驱动电压、电流效率和量子效率,并且测量了在10mA/cm2的电流密度下亮度变为初始亮度的95%时的时间,结果在下表1中示出。
[表1]
如表1中所示,可以确定使用本公开内容的由化学式1表示的化合物作为发光层的掺杂剂的有机发光器件在寿命方面表现出优异的特性。
[附图标记说明]
1:基底 2:阳极
3:发光层 4:阴极
5:空穴注入层 6:空穴传输层
7:发光层 8:电子传输层
Claims (15)
1.一种由以下化学式1表示的化合物:
[化学式1]
在所述化学式1中,
R为Si(R1)(R2)(R3),
R1至R3各自独立地为C6-20芳基,
L1为单键;亚苯基;或者萘二基,
m和n各自独立地为0至3的整数,
R4和R5各自独立地为氢;或氘,
Ar3为经C1-10烷基取代或未经取代的C6-20芳基,
Ar1和Ar2各自独立地为C1-10烷基;C6-20芳基;或者彼此连接以形成由以下化学式2表示的取代基,
[化学式2]
在所述化学式2中,
p和q各自独立地为0至4的整数,
R6和R7各自独立地为氢;或氘。
2.根据权利要求1所述的化合物,
其中所述化学式1由以下化学式中的任一者表示:
[化学式1-1]
[化学式1-2]
[化学式1-5]
在所述化学式中,
R8和R9各自独立地为氢,
m、n、p、q、R、R4至R7、L1和Ar3如权利要求1中所限定。
3.根据权利要求1所述的化合物,
其中R1至R3各自独立地为苯基。
4.根据权利要求1所述的化合物,
其中R1至R3中的至少一者为苯基。
5.根据权利要求1所述的化合物,
其中L1为单键;或者亚苯基。
6.根据权利要求1所述的化合物,
其中m和n二者均为0。
7.根据权利要求1所述的化合物,
其中R6和R7各自独立地为氢。
8.根据权利要求1所述的化合物,
其中Ar3为未经取代或经C1-10烷基取代的苯基;或者萘基。
9.根据权利要求1所述的化合物,
其中由所述化学式1表示的所述化合物为选自以下化合物中的一者:
10.一种有机发光器件,包括第一电极;与所述第一电极相对的第二电极;以及在所述第一电极与所述第二电极之间的一个或更多个有机材料层,其中一个或更多个所述有机材料层包含根据权利要求1至9中任一项所述的化合物。
11.根据权利要求10所述的有机发光器件,
其中包含所述化合物的所述有机材料层为发光层。
12.根据权利要求11所述的有机发光器件,
其中所述发光层还包含由以下化学式3表示的化合物:
[化学式3]
/>
在所述化学式3中,
L2为单键;或者经取代或未经取代的C6-60亚芳基,
Ar4和Ar5各自独立地为经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含选自N、O和S中的一个或更多个杂原子的C5-60杂芳基。
13.根据权利要求12所述的有机发光器件,
其中L2为单键;或者亚苯基。
14.根据权利要求12所述的有机发光器件,
其中Ar4和Ar5各自独立地为选自以下中的一者:
15.根据权利要求12所述的有机发光器件,
其中由所述化学式3表示的所述化合物为选自以下化合物中的一者:
/>
/>
/>
/>
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104768940A (zh) * | 2012-11-02 | 2015-07-08 | 出光兴产株式会社 | 有机电致发光元件 |
CN106206999A (zh) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | 有机发光器件 |
CN106206964A (zh) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | 有机发光器件 |
CN107868097A (zh) * | 2016-09-22 | 2018-04-03 | 三星显示有限公司 | 胺化合物和包括其的有机电致发光器件 |
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US9748492B2 (en) * | 2012-11-02 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
KR102083984B1 (ko) | 2013-01-28 | 2020-04-16 | 삼성디스플레이 주식회사 | 실리콘계 화합물 및 이를 포함한 유기 발광 소자 |
KR102289321B1 (ko) | 2013-07-10 | 2021-08-11 | 에스케이머티리얼즈제이엔씨 주식회사 | 환축합 플루오렌 화합물 또는 플루오렌 화합물을 포함하는 발광보조층용 재료 |
KR20150014778A (ko) | 2013-07-30 | 2015-02-09 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US10950803B2 (en) | 2014-10-13 | 2021-03-16 | Universal Display Corporation | Compounds and uses in devices |
US10381569B2 (en) * | 2014-11-25 | 2019-08-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20160141361A (ko) * | 2015-05-27 | 2016-12-08 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102630643B1 (ko) | 2015-05-27 | 2024-01-31 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US11081647B2 (en) | 2016-04-22 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102093535B1 (ko) | 2016-04-25 | 2020-03-25 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR20180099965A (ko) | 2017-02-27 | 2018-09-06 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
-
2018
- 2018-10-16 KR KR1020180123388A patent/KR102241368B1/ko active IP Right Grant
-
2019
- 2019-09-30 WO PCT/KR2019/012738 patent/WO2020080702A1/ko active Application Filing
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104768940A (zh) * | 2012-11-02 | 2015-07-08 | 出光兴产株式会社 | 有机电致发光元件 |
CN106206999A (zh) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | 有机发光器件 |
CN106206964A (zh) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | 有机发光器件 |
CN107868097A (zh) * | 2016-09-22 | 2018-04-03 | 三星显示有限公司 | 胺化合物和包括其的有机电致发光器件 |
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