CN107108529B - 有机电致发光元件 - Google Patents
有机电致发光元件 Download PDFInfo
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- CN107108529B CN107108529B CN201580069279.1A CN201580069279A CN107108529B CN 107108529 B CN107108529 B CN 107108529B CN 201580069279 A CN201580069279 A CN 201580069279A CN 107108529 B CN107108529 B CN 107108529B
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- 239000010410 layer Substances 0.000 claims abstract description 146
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 9
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- 229910052701 rubidium Inorganic materials 0.000 claims description 3
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- 125000001424 substituent group Chemical group 0.000 description 19
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- 125000005843 halogen group Chemical group 0.000 description 4
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
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- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 125000005264 aryl amine group Chemical group 0.000 description 2
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical class CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 229910001573 adamantine Inorganic materials 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000006193 alkinyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
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- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
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Abstract
本发明提供一种有机电致发光元件,其包含阳极、阴极、以及存在于上述阳极与阴极之间的有机物层,上述有机物层包含选自由空穴注入层、空穴传输层、发光层、寿命改善层、电子传输层和电子注入层组成的组中的1种以上。
Description
技术领域
本发明涉及包含有机物层的有机电致发光元件。
背景技术
自从1965年利用蒽单晶的蓝色电发光,一直进行对有机电致发光(electroluminescent,EL)元件的研究,后来1987年由唐(Tang)提出了由空穴层(NPB)和发光层(Alq3)构成的2层结构的有机电致发光元件。之后,为了实现有机电致发光元件的高效率、长寿命特性,提出了在元件内负责空穴注入或空穴传输的有机层、在元件内负责电子注入或电子传输的有机层、诱导通过空穴和电子的结合而发生电致发光的有机层等多层结构的形态。多层结构的导入将有机电致发光元件的性能提高至商用化特性,从1997年车辆用收音机显示器制品开始,其应用范围扩大至便携式信息显示装置以及TV用显示器。
显示器的大型化、高分辨率化的要求赋予了有机电致发光元件的高效率化、长寿命化的课题。特别是,通过在相同面积上形成更多的像素而实现的高分辨率化的情况下,导致减少有机电致发光元件的发光面积的结果,从而只能减少寿命,成为了有机电致发光元件需要克服的最重要的技术课题。
有机电致发光元件在两电极施加电流或电压时,空穴从阳极注入至有机物层,电子从阴极注入至有机物层。注入的空穴与电子相遇时形成激子(exciton),该激子跃迁至基态而发出光。此时,有机电致发光元件可以根据形成的激子的电子自旋种类而分成单重态激子对发光做出贡献的荧光电致发光元件和三重态激子对发光做出贡献的磷光电致发光元件。
通过电子与空穴的再结合而形成的激子的电子自旋是单重态激子与三重态激子以25%、75%的比例生成的。通过单重态激子而进行发光的荧光电致发光元件根据生成比例在理论上认为内部量子效率不可能超过25%,外部量子效率的临界为5%。通过三重态激子而形成发光的磷光电致发光元件与荧光电致发光元件相比,能够将发光效率提高至最大4倍。
如上所述,磷光电致发光元件以理论上的事实为依据在发光效率方面显示出比荧光电致发光元件高的效率,但是在蓝色磷光电致发光元件中,对于满足深蓝色的色纯度和高效率的主体的开发不足,目前为止,与蓝色磷光电致发光元相比,蓝色荧光电致发光元件主要用于制品。
另一方面,报道了为了提高有机电致发光元件的特性,通过防止空穴扩散至电子传输层,从而提高元件的稳定性的研究结果。公开了通过在发光层与电子传输层之间使用BCP或BPhen等材料,从而阻止空穴向电子传输层扩散,并限制在发光层内,以提高空穴与电子的再结合效率的技术。但是,BCP或BPhen等的衍生物对空穴的氧化稳定性降低,对热的耐久性脆弱,结果,减少有机电致发光元件的寿命而不能商业化。另外,这样的材料阻碍电子的移动而升高有机电致发光元件的驱动电压。
发明内容
技术课题
为了解决上述问题,本发明的目的是提供驱动电压、发光效率和寿命优异的有机电致发光元件。
解决课题方法
为了实现上述目的,本发明提供一种有机电致发光元件,其包含阳极、阴极、以及存在于上述阳极与阴极之间的有机物层,上述有机物层包含由下述化学式1表示的化合物。
[化学式1]
在上述化学式1中,
Ra和Rb彼此相同或不同,且各自独立地选自由C1~C40的烷基和C6~C60的芳基组成的组中,或者彼此结合而形成稠环,
R1至R3彼此相同或不同,且各自独立地选自由氢、氘、卤素基团、氰基、硝基、氨基、C1~C40的烷基、C2~C40的烯基、C2~C40的炔基、C3~C40的环烷基、原子核数3至40的杂环烷基、C6~C60的芳基、原子核数5至60的杂芳基、C1~C40的烷氧基、C6~C60的芳氧基、C1~C40的烷基甲硅烷基、C6~C60的芳基甲硅烷基、C1~C40的烷基硼基、C6~C60的芳基硼基、C1~C40的膦基、C1~C40的氧化膦基和C6~C60的芳基胺基组成的组中,或者与邻接的基团结合而形成稠环,
L为单键、或者选自由C6~C18的亚芳基和原子核数5至18的杂亚芳基组成的组中,
Z1至Z5彼此相同或不同,且各自独立地为N或C(R4),此时至少一个为N,当所述C(R4)为多个时,多个C(R4)彼此相同或不同,
c和e各自为0至4的整数,
d为0至3的整数,
m和n各自为1至3的整数,
上述R4选自由氢、氘、卤素基团、氰基、硝基、氨基、C1~C40的烷基、C2~C40的烯基、C2~C40的炔基、C3~C40的环烷基、原子核数3至40的杂环烷基、C6~C60的芳基、原子核数5至60的杂芳基、C1~C40的烷氧基、C6~C60的芳氧基、C1~C40的烷基甲硅烷基、C6~C60的芳基甲硅烷基、C1~C40的烷基硼基、C6~C60的芳基硼基、C1~C40的膦基、C1~C40的氧化膦基和C6~C60的芳基胺基组成的组中,或者与邻接的基团结合而形成稠环,
上述Ra、Rb的烷基、芳基和上述R1至R4的烷基、烯基、炔基、环烷基、杂环烷基、芳基、杂芳基、烷氧基、芳氧基、烷基甲硅烷基、芳基甲硅烷基、烷基硼基、芳基硼基、膦基、氧化膦基、芳基胺基及上述L的亚芳基、杂亚芳基各自独立地被选自由氘、卤素基团、氰基、硝基、氨基、C1~C40的烷基、C2~C40的烯基、C2~C40的炔基、C3~C40的环烷基、原子核数3至40的杂环烷基、C6~C60的芳基、原子核数5至60的杂芳基、C1~C40的烷氧基、C6~C60的芳氧基、C1~C40的烷基甲硅烷基、C6~C60的芳基甲硅烷基、C1~C40的烷基硼基、C6~C60的芳基硼基、C1~C40的膦基、C1~C40的氧化膦基和C6~C60的芳基胺基组成的组中的1种以上的取代基所取代或未取代,当上述取代基为多个时,多个取代基彼此相同或不同。
这样的由化学式1表示的化合物可以包含在上述有机物层中的寿命改善层。
发明效果
本发明通过将包含具有特定物性的化合物的寿命改善层、电子传输层或电子注入层导入有机电致发光元件,可以提供驱动电压、发光效率和寿命优异的有机电致发光元件。
另外,通过将本发明的有机电致发光元件应用于显示面板,可以提供性能和寿命得到提高的显示面板。
附图说明
图1是表示根据本发明的一个实施方式的有机电致发光元件的截面图。
具体实施方式
下面,说明本发明。
本发明的一个实施方式提供一种有机电致发光元件,其包含阳极、阴极、以及存在于上述阳极与阴极之间的有机物层,上述有机物层包含由下述化学式1表示的化合物。
[化学式1]
在上述化学式1中,
Ra和Rb彼此相同或不同,且各自独立地选自由C1~C40的烷基和C6~C60的芳基组成的组中,或者彼此结合而形成稠环,
R1至R3彼此相同或不同,且各自独立地选自由氢、氘、卤素基团、氰基、硝基、氨基、C1~C40的烷基、C2~C40的烯基、C2~C40的炔基、C3~C40的环烷基、原子核数3至40的杂环烷基、C6~C60的芳基、原子核数5至60的杂芳基、C1~C40的烷氧基、C6~C60的芳氧基、C1~C40的烷基甲硅烷基、C6~C60的芳基甲硅烷基、C1~C40的烷基硼基、C6~C60的芳基硼基、C1~C40的膦基、C1~C40的氧化膦基和C6~C60的芳基胺基组成的组中,或者与邻接的基团结合(具体而言,邻接的R1彼此结合、邻接的R2彼此结合、邻接的R3彼此结合、或者R1与R2的结合)而形成稠环,
L为单键、或者选自由C6~C18的亚芳基和原子核数5至18的杂亚芳基组成的组中,
Z1至Z5彼此相同或不同,且各自独立地为N或C(R4),此时至少一个为N,当所述C(R4)为多个时,多个C(R4)彼此相同或不同,
c和e各自为0至4的整数,
d为0至3的整数,
m和n各自为1至3的整数,
上述R4选自由氢、氘、卤素基团、氰基、硝基、氨基、C1~C40的烷基、C2~C40的烯基、C2~C40的炔基、C3~C40的环烷基、原子核数3至40的杂环烷基、C6~C60的芳基、原子核数5至60的杂芳基、C1~C40的烷氧基、C6~C60的芳氧基、C1~C40的烷基甲硅烷基、C6~C60的芳基甲硅烷基、C1~C40的烷基硼基、C6~C60的芳基硼基、C1~C40的膦基、C1~C40的氧化膦基和C6~C60的芳基胺基组成的组中,或者与邻接的基团结合(具体而言,邻接的R4彼此结合)而形成稠环,
上述Ra、Rb的烷基、芳基和上述R1至R4的烷基、烯基、炔基、环烷基、杂环烷基、芳基、杂芳基、烷氧基、芳氧基、烷基甲硅烷基、芳基甲硅烷基、烷基硼基、芳基硼基、膦基、氧化膦基、芳基胺基及上述L的亚芳基、杂亚芳基各自独立地被选自由氘、卤素基团、氰基、硝基、氨基、C1~C40的烷基、C2~C40的烯基、C2~C40的炔基、C3~C40的环烷基、原子核数3至40的杂环烷基、C6~C60的芳基、原子核数5至60的杂芳基、C1~C40的烷氧基、C6~C60的芳氧基、C1~C40的烷基甲硅烷基、C6~C60的芳基甲硅烷基、C1~C40的烷基硼基、C6~C60的芳基硼基、C1~C40的膦基、C1~C40的氧化膦基和C6~C60的芳基胺基组成的组中的1种以上的取代基所取代或未取代,当上述取代基为多个时,多个取代基彼此相同或不同。
图1中图示了根据本发明的一个实施方式的有机电致发光元件。根据本发明的一个实施方式,有机电致发光元件包含阳极100、阴极200、以及存在于上述阳极与阴极之间的有机物层300。
阳极100起到将空穴注入有机物层300的作用。构成阳极100的物质没有特别限定,作为非限制性例子,可举出钒、铬、铜、锌、金等金属;它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO与Al、SnO2与Sb等金属与氧化物的组合;聚噻吩、聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDT)、聚吡咯、聚苯胺等导电性高分子;以及炭黑。制造阳极100的方法也没有特别限定,作为非限制性例子,可举出在由硅晶片、石英、玻璃板、金属板或塑料膜构成的基板上涂覆阳极物质的方法。
阴极200起到将电子注入有机物层300的作用。构成阴极200的物质没有特别限定,作为非限制性例子,可举出镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡、铅等金属;它们的合金;以及LiF/Al、LiO2/Al等多层结构物质。制造阴极200的方法也只要是本领域中公知的方法就没有特别限定。
如图1所示,有机物层300优选包含选自由空穴注入层301、空穴传输层302、发光层303、寿命改善层304、电子传输层305和电子注入层306组成的组中的1种以上。考虑有机电致发光元件的特性时,有机物层300更优选将上述层全部包含。
空穴注入层301和空穴传输层302起到使从阳极100注入的空穴移动至发光层303的作用。构成空穴注入层301和空穴传输层302的物质只要是空穴注入势垒低且空穴迁移率大的物质,就没有特别限定,作为非限制性例子,可举出芳基胺衍生物。
发光层303是空穴和电子相遇而形成激子(exciton)的层。根据构成发光层303的物质,有机电致发光元件所发出的光的颜色有可能不同。发光层303可以包含主体和掺杂剂,优选主体包含70至99.9重量%,掺杂剂包含0.1至30重量%。发光层303为蓝色荧光、绿色荧光或红色荧光时,优选主体包含70至99.9重量%,掺杂剂包含0.1至30重量%,更优选主体包含80至99重量%,掺杂剂包含1至20重量%。
上述发光层303中包含的主体只要是本领域中公知的主体,就没有特别限定,作为非限制性例子,可举出碱金属络合物、碱土金属络合物、或者芳香族稠环衍生物。特别是,作为主体,优选使用能够提高有机电致发光元件的发光效率和寿命的铝络合物、铍络合物、蒽衍生物、芘衍生物、苯并菲衍生物、咔唑衍生物、二苯并呋喃衍生物、二苯并噻吩衍生物。
上述发光层303中所包含的掺杂剂只要是本领域中公知的掺杂剂,就没有特别限定,作为非限制性例子,可举出蒽衍生物、芘衍生物、芳基胺衍生物、包含铱(Ir)或铂(Pt)的金属络合物。
发光层303可以由一层(单层)形成,或者由多个层(多层)形成。发光层303由多个层形成的情况下,有机电致发光元件可以发出多种颜色的光。例如,可以在空穴传输层302与寿命改善层304之间具备多个发光层而提供带有混合色的有机电致发光元件。此时,发光层可以由异种材料构成。另外,发光层303由多个层形成的情况下,虽然驱动电压变大,但有机电致发光元件内的电流值变得恒定,从而可以提供与发光层的数量相应地提高了发光效率的有机电致发光元件。
寿命改善层304用于提高有机电致发光元件的寿命,配置在发光层303与电子传输层305之间。形成寿命改善层304的物质没有特别限定,优选同时具有吸电子性大的吸电子基团(EWG)和供电子性大的供电子基团(EDG)的显示双极性(bipolar)的化合物。特别是,更优选形成寿命改善层304的物质为由上述化学式1表示的化合物。
具体而言,上述双极性化合物优选电离势(ionization potenitial)为5.5eV以上,更优选为5.5至7.0eV,最优选为5.6至6.6eV。另外,上述双极性化合物优选HOMO值与LUMO值之差(EHOMO-ELUMO)大于3.0eV,更优选为2.8至3.8eV。另外,上述双极性化合物优选三重态能量为2.3eV以上,更优选为2.3至3.5eV,最优选为2.3至3.0eV。上述双极性化合物优选单重态能量与三重态能量之差小于0.7eV,更优选为0.01至0.7eV。将电离势为5.5eV以上的化合物用于寿命改善层304时,可以防止空穴向电子传输层305扩散或移动,从而能够提高有机电致发光元件的寿命。
一般来说,空穴在有机电致发光元件内随着电离势水平而移动,空穴越过发光层303而向电子传输层305扩散或移动时,发生氧化引起的非可逆性分解反应,从而导致有机电致发光元件的寿命降低。但是,在本发明的一个实施方式中,由于由电离势为5.5eV以上的双极性化合物形成的寿命改善层304,从而防止空穴向电子传输层305扩散或移动,因此能够改善有机电致发光元件的寿命。即,空穴被寿命改善层304的高能量势垒所阻碍而不能向电子传输层305扩散或移动,停留在发光层303。
发光层303由红色磷光物质构成的情况下,只要上述寿命改善层304所包含的双极性化合物的电离势为5.5eV以上即可,但由绿色磷光物质或蓝色磷光物质构成的情况下,优选双极性化合物的电离势为6.0eV以上。
另一方面,上述双极性化合物优选HOMO值与LUMO值之差(EHOMO-ELUMO)超过3.0eV、三重态能量为2.3eV、单重态能量与三重态能量之差小于0.7eV。这是因为将这样的化合物用于寿命改善层304时,可以防止在发光层303中形成的激子向电子传输层305扩散,还能够阻止在发光层303与电子传输层305的界面产生发光的现象。结果,由此可以防止有机电致发光元件的光谱混色,并提高稳定性,从而可以提高有机电致发光元件的寿命。
在本发明的一个实施方式中,双极性化合物同时具有吸电子性大的吸电子基团(EWG)和供电子性大的供电子基团(EDG),从而具有HOMO和LUMO的电子云分离的特征。因此,化合物的三重态能量与单重态能量之差(ΔEst)小于0.7eV而较少,所以即使HOMO值与LUMO值之差(EHOMO-ELUMO)超过3.0eV,也能够具有高的三重态能量(T1)。
发光层303由红色磷光物质形成的情况下,只要上述寿命改善层304中包含的双极性化合物的三重态能量为2.3eV以上即可,但由绿色磷光物质形成的情况下,优选为2.5eV以上,由蓝色磷光物质形成的情况下,优选为2.7eV以上。
另一方面,优选上述双极性化合物的空穴迁移率和电子迁移率在常温为1×10- 6cm2/V·s以上。这是因为将这样的化合物用于寿命改善层304时,防止电子的注入比从阳极100注入的空穴的数量少,从而能够提高有机电致发光元件的寿命。
由于从阳极100注入的空穴的数量与从阴极200注入的电子的数量之差而导致电子与空穴不均衡的情况下,没能够通过再结合而形成激子的电子或空穴会堆积在发光层303。堆积在上述发光层303的电子或空穴导致在发光层303不能顺利地进行氧化和还原,或者对邻接的层造成影响而减少有机电致发光元件的寿命。
但是,本发明的寿命改善层304中所包含的双极性化合物由于供电子基团(EDG)而空穴的迁移率在常温显示1×10-6cm2/V·s以上,由于吸电子基团(EWG)而电子迁移率在常温显示1×10-6cm2/V·s以上。将这样的化合物用于寿命改善层304时,能够将电子有效地注入发光层303。像这样顺利地向发光层303注入电子时,在发光层303中激子的形成效率提高,从而能够改善有机电致发光元件的寿命。
上述双极性化合物优选作为供电子基团(EDG)的芴基和作为吸电子基团(EWG)的6元杂环通过连接基团(亚苯基、亚联苯基或亚三联苯基)结合而形成基本骨架。此时,作为上述双极性化合物,例如可以为由上述化学式1表示。
在本发明的一个实施方式中,寿命改善层304、电子传输层30和电子注入层306中的至少一个包含由上述化学式1表示的化合物。
另外,由上述化学式1表示的化合物可以为由下述化学式2至4表示的化合物中的任一种。
[化学式2]
[化学式3]
[化学式4]
在上述化学式2至4中,
Ra、Rb、R1至R3、Z1至Z5、c、d和e各自与上述化学式1中的定义相同。
在上述C-1至C-15中,
R4与上述化学式1中的定义相同,多个R4彼此相同或不同,
R5选自由氢、氘、卤素、氰基、硝基、C1~C40的烷基、C2~C40的烯基、C2~C40的炔基、C3~C40的环烷基、原子核数3至40的杂环烷基、C6~C60的芳基、原子核数5至60的杂芳基、C6~C60的芳氧基、C1~C40的烷氧基、C6~C60的芳基胺基、C1~C40的烷基甲硅烷基、C1~C40的烷基硼基、C6~C60的芳基硼基、C6~C60的芳基膦基、C6~C60的芳基氧化膦基和C6~C60的芳基甲硅烷基组成的组中,或者与邻接的基团结合(具体而言,邻接的R5彼此结合、或者R4与R5的结合)而形成稠环,
p为1至4的整数,
上述R5的烷基、烯基、炔基、环烷基、杂环烷基、芳基、杂芳基、芳氧基、烷氧基、芳基胺基、烷基甲硅烷基、烷基硼基、芳基硼基、芳基膦基、芳基氧化膦基和芳基甲硅烷基各自独立地被选自由氘、卤素基团、氰基、硝基、C1~C40的烷基、C2~C40的烯基、C2~C40的炔基、C6~C60的芳基、原子核数5至60的杂芳基、C6~C60的芳氧基、C1~C40的烷氧基、C6~C60的芳基胺基、C3~C40的环烷基、原子核数3至40的杂环烷基、C1~C40的烷基甲硅烷基、C1~C40的烷基硼基、C6~C60的芳基硼基、C6~C60的芳基膦基、C6~C60的芳基氧化膦基和C6~C60的芳基甲硅烷基组成的组中的1种以上的取代基所取代或未取代,此时,当上述取代基为多个时,多个取代基彼此相同或不同。
[化学式5]
上述化学式5中,
Ra、Rb、R1至R4、L、c、d、e、m和n各自与上述化学式1中的定义相同。在这里,考虑有机电致发光元件的特性时,在由上述化学式5表示的化合物中,上述R4优选彼此相同。即,优选R4相同并形成对称结构。
此外,在本发明的由化学式1表示的化合物中,R1至R3优选各自独立地选自由氢、氘、C1~C40的烷基、C6~C60的芳基、原子核数5至60的杂芳基和C6~C60的芳基胺基组成的组中。另外,m和n各自为1至3的整数,m优选为1,n优选为1或2。
另外,在本发明的由化学式1表示的化合物中,上述L优选为单键、亚苯基、亚联苯基或亚三联苯基。具体而言,作为连接基团的L优选选自由下述L-1至L-9所表示的结构(*为形成键的部位)组成的组中。
这样的本发明的由化学式1表示的化合物可以利用由下述化学式LE-01至LE-12表示的化合物而进一步具体化。
在本发明中,“烷基”是指来自碳原子数1至40的直链或支链的饱和烃的1价取代基。作为这样的烷基的例子,可举出甲基、乙基、丙基、异丁基、仲丁基、戊基、异戊基、己基等,但并不限定于此。
在本发明中,“烯基(alkenyl)”是指来自具有1个以上碳-碳双键的碳原子数2至40的直链或支链的不饱和烃的1价的取代基。作为这样的烯基的例子,可举出乙烯基(vinyl)、烯丙基(allyl)、异丙烯基(isopropenyl)、2-丁烯基(2-butenyl)等,但不限于此。
在本发明中,“炔基(alkynyl)”是指来自具有1个以上碳-碳三键的碳原子数2至40的直链或支链的不饱和烃的1价的取代基。作为这样的炔基的例子,可举出乙炔基(ethynyl)、2-丙炔基(2-propynyl)等,但不限于此。
在本发明中,“芳基”是指来自单环或2个以上的环组合而成的碳原子数6至60的芳香族烃基的1价的取代基。另外,还可以包含2个以上的环彼此单纯附着(pendant)或缩合的形态。作为这样的芳基的例子,可举出苯基、萘基、菲基、蒽基等,但不限于此。
在本发明中,“杂芳基”是指来自原子核数5至60的单杂环或多杂环芳香族烃的1价的取代基。此时,环中的一个以上的碳、优选为1至3碳被N、O、S或Se之类的杂原子所取代。另外,还可以包含2个以上的环彼此单纯附着(pendant)或缩合的形态,进而还可以包含与芳基缩合的形态。作为这样的杂芳基的例子,可举出吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基之类的六元单环;吩噻吩基(phenoxathienyl)、吲哚嗪基(indolizinyl)、吲哚基(indolyl)、嘌呤基(purinyl)、喹啉基(quinolyl)、苯并噻唑基(benzothiazole)、咔唑基(carbazolyl)之类的多环;以及2-呋喃基;N-咪唑基;2-异唑基;2-吡啶基;2-嘧啶基等,但不限于此。
在本发明中,“芳氧基”是指由RO-表示的1价的取代基,上述R为碳原子数6至60的芳基,作为这样的芳氧基的例子,可举出苯氧基、萘氧基、二苯氧基等,但不限于此。
在本发明中,“烷氧基”是指由R'O-表示的1价的取代基,上述R'为碳原子数1至40的烷基。这样的烷氧基可以包含直链(linear)、支链(branched)或环(cyclic)结构,作为例子,可举出甲氧基、乙氧基、正丙氧基、1-丙氧基、叔丁氧基、正丁氧基、戊氧基等,但不限于此。
在本发明中,“芳基胺”是指被碳原子数6至60的芳基所取代的胺。
在本发明中,“环烷基”是指来自碳原子数3至40的单环或多环非芳香族烃的1价的取代基。作为这样的环烷基的例子,可举出环丙基、环戊基、环己基、降冰片基(norbornyl)、金刚烷基(adamantine)等,但不限于此。
在本发明中,“杂环烷基”是指来自原子核数3至40的非芳香族烃的1价的取代基,环中的一个以上的碳、优选为1至3个碳被N、O、S或Se之类的杂原子所取代。作为这样的杂环烷基的例子,可举出吗啉基、哌嗪基等,但不限于此。
在本发明中,“烷基甲硅烷基”是指被碳原子数1至40的烷基所取代的甲硅烷基,“芳基甲硅烷基”是指被碳原子数5至40的芳基所取代的甲硅烷基。
在本发明中,“稠环”是指缩合脂肪族环、缩合芳香族环、缩合脂肪族杂环、缩合芳香族杂环或它们的组合的形态。
这样的本发明的由化学式1表示的化合物可以参考下述实施例的合成步骤而多样地进行合成。
电子传输层305和电子注入层306起到使从阴极200注入的电子向发光层303移动的作用。构成电子传输层305和电子注入层306的物质只要是电子注入容易且电子迁移率大的物质,就没有特别限定,作为非限制性例子,可举出由上述化学式1表示的化合物、蒽衍生物、杂芳香族化合物、碱金属络合物。
具体而言,上述电子传输层305和/或电子注入层306由与上述寿命改善层304相同的物质,即由上述化学式1表示的化合物形成。另外,为了使电子从阴极容易地注入,电子传输层305和/或电子注入层306还可以使用共蒸镀有碱金属络合物的层。作为上述碱金属络合物,可举出碱金属、碱土金属或稀土类金属。
这样的根据本发明的一个实施方式的有机物层300可以在空穴传输层302与发光层303之间进一步包含阻挡电子和激子的有机膜层(未图示)。由于有机膜层具有高LUMO值,可以阻止电子向空穴传输层302移动,由于具有高三重态能量,可以防止发光层303的激子向空穴传输层302扩散。形成有机膜层的物质没有特别限定,作为非限制性的例子,可举出咔唑衍生物或芳基胺衍生物。
制造根据本发明的一个实施方式的有机物层300的方法没有特别限制,作为非限制性的例子,可举出真空蒸镀法、溶液涂布法。作为上述溶液涂布法的例子,可举出旋涂法、浸涂法、刮涂法、喷墨印刷法、热转印方法等。
以上的根据本发明的一个实施方式的有机电致发光元件具有依次层叠有阳极100、有机物层300和阴极200的结构,在阳极100与有机物层300之间或者阴极200与有机物层300之间还可以包含绝缘层或粘接层。这样的有机电致发光元件在施加电压和电流时能够维持最大发光效率并增加初始亮度的半衰期(Life time),因此寿命特性优异。
以下,通过实施例详细说明本发明,但下述实施例仅是例示本发明,本发明不受下述实施例的限定。
[准备例1至12]准备化合物LE-01至LE-12
作为本发明的双极性化合物,准备由下述LE-01至LE-12表示的化合物,利用本领域公知的方法分别测定ΔEst、三重态能量、电离势、EHOMO-ELUMO、电子迁移率和空穴迁移率,并示于下述表1。
[表1]
[实施例1至12]蓝色荧光有机电致发光元件的制造
将以厚度薄膜涂覆有ITO(Indium tin oxide,氧化铟锡)的玻璃基板用蒸馏水进行超声波清洗。蒸馏水清洗结束后,用异丙醇、丙酮、甲醇等溶剂进行超声波清洗并干燥后,移送至UV OZONE清洗机(Power sonic 405,Hwasin Tech),然后利用UV将上述基板清洗5分钟,将基板移送至真空蒸镀机。
在如上所述准备的ITO透明电极(基板)上依次蒸镀空穴注入层、空穴传输层、发光层、寿命改善层、电子传输层、电子注入层和阴极而制造元件。制造的元件的结构如下述表2所示。
[表2]
在上述表2中,NPB、AND和Alq3的结构如下。
[比较例1]蓝色荧光有机电致发光元件的制造
不使用寿命改善层,将电子传输层蒸镀成30nm,除此之外,用与实施例1相同的步骤制造了元件。
[比较例2]蓝色荧光有机电致发光元件的制造
代替LE-01而使用下述结构的BCP,除此之外,用与实施例1相同的步骤制造了元件。
[实验例1]
对上述实施例1至12和比较例1、2中制造的各个元件测定电流密度为10mA/cm2时的驱动电压、电流效率、发光波长和寿命(T97),将其结果示于下述表3。
[表3]
观察上述表3,可以确认包含本发明的寿命改善层的实施例1至12的有机电致发光元件与比较例1和2的有机电致发光元件相比,电流效率、驱动电压以及寿命优异。
[实施例13至20]绿色磷光有机电致发光元件的制造
将以厚度薄膜涂覆有ITO(Indium tin oxide,氧化铟锡)的玻璃基板用蒸馏水进行超声波清洗。蒸馏水清洗结束后,用异丙醇、丙酮、甲醇等溶剂进行超声波清洗并干燥后,移送至UV OZONE清洗机(Power sonic 405,Hwasin Tech),然后利用UV将上述基板清洗5分钟,将基板移送至真空蒸镀机。
在如上所述准备的ITO透明电极(基板)上依次蒸镀空穴注入层、空穴传输层、发光层、寿命改善层、电子传输层、电子注入层和阴极而制造元件。制造的元件的结构如下述表4所示。
[表4]
在上述表4中,m-MTDATA、TCTA、Ir(ppy)3和CBP的结构如下。
[比较例3]绿色磷光有机电致发光元件的制造
不使用寿命改善层,将电子传输层蒸镀成30nm,除此之外,用与实施例13相同的步骤制造了元件。
[比较例4]绿色磷光有机电致发光元件的制造
代替LE-01而使用下述结构的BCP,除此之外,用与实施例13相同的步骤制造了元件。
[实验例2]
对上述实施例13至20和比较例3、4中制造的各个元件测定电流密度为10mA/cm2时的驱动电压、电流效率、发光波长和寿命(T97),将其结果示于下述表5。
[表5]
观察上述表5,可以确认包含本发明的寿命改善层的实施例13至20的有机电致发光元件与比较例3和4的有机电致发光元件相比,电流效率、驱动电压以及寿命优异。
Claims (12)
2.根据权利要求1所述的有机电致发光元件,所述有机物层还包含选自空穴注入层、空穴传输层和电子注入层中的1种以上,
所述电子传输层和所述电子注入层中的至少一层包含由所述化学式5表示的化合物。
3.根据权利要求1所述的有机电致发光元件,所述发光层由绿色磷光物质形成,所述寿命改善层中所包含的由所述化学式5表示的化合物的电离势为6.0eV以上,三重态能量为2.5eV以上。
4.根据权利要求1所述的有机电致发光元件,所述发光层由蓝色磷光物质形成,所述寿命改善层中所包含的由所述化学式5表示的化合物的电离势为6.0eV以上,三重态能量为2.7eV以上。
5.根据权利要求2所述的有机电致发光元件,所述电子传输层包含由所述化学式5表示的化合物,
所述电子传输层和寿命改善层的化合物为彼此相同的化合物。
6.根据权利要求2所述的有机电致发光元件,所述电子注入层包含由所述化学式5表示的化合物,所述电子注入层和寿命改善层的化合物为彼此相同的化合物。
7.根据权利要求1所述的有机电致发光元件,由所述化学式5表示的化合物的HOMO值与LUMO值之差大于3.0eV,三重态能量为2.3eV以上,单重态能量与三重态能量之差小于0.7eV。
8.根据权利要求1所述的有机电致发光元件,由所述化学式5表示的化合物的电子迁移率和空穴迁移率在常温时为1×10-6cm2/V·s以上。
10.根据权利要求1所述的有机电致发光元件,所述Ra和Rb彼此相同或不同,且各自独立地为甲基或苯基。
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