CN106414450B - 化合物、有机光电装置以及显示装置 - Google Patents
化合物、有机光电装置以及显示装置 Download PDFInfo
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- CN106414450B CN106414450B CN201580030598.1A CN201580030598A CN106414450B CN 106414450 B CN106414450 B CN 106414450B CN 201580030598 A CN201580030598 A CN 201580030598A CN 106414450 B CN106414450 B CN 106414450B
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl 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
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 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
- 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
本发明涉及一种化合物、有机光电装置以及显示装置。其中,所述化合物由化学式1表示,由化学式1表示的化合物能够实现有机光电装置具有诸如高效率、长使用寿命的特征。化学式1与实施方式中所定义的相同。
Description
技术领域
本发明涉及化合物、有机光电装置以及显示装置。
背景技术
有机光电装置(organic optoelectronic diode)为将电能转换成光能的装置,且也为将光能转换成电能的装置。
有机光电装置可根据其驱动原理分类如下。一种为光电装置,其中激子(exciton)通过光能产生,分离成电子及空穴且电子及空穴传递至不同电极以产生电能;且另一种为发光装置,其中将电压或电流供应至电极以自电能产生光能。
有机光电装置的实例可为有机光电器件、有机发光二极管、有机太阳能电池以及有机感光鼓(organic photo conductor drum)。
其中,有机发光二极管(organic light emitting diode;OLED)近来已由于对平板显示器(flatpanel display device)的要求增加而获得关注。此类有机发光二极管通过施加电流至有机发光材料而将电能转换成光。其具有在阳极(anode)与阴极(cathode)之间插入有机层的结构。在本文中,有机层可包含发射层及视情况存在的辅助层,且辅助层可包含例如选自空穴注入层、空穴传输层、电子阻挡层、电子传输层、电子注入层以及空穴阻挡层中的至少一者以便增加有机发光二极管的效率及稳定性。
有机发光二极管的效能可受有机层的特征影响,且其中,可主要受有机层的有机材料的特征影响。
具体言之,需要开发能够增加空穴及电子迁移率且同时增加电化学稳定性的有机材料,使得有机发光二极管可应用于大规模平板显示器。
发明的详细说明
发明内容
提供用于有机光电装置的化合物,所述化合物能够实现有机光电装置具有诸如高效率、长使用寿命以及其类似物的特征。
提供有机光电装置及包含用于有机光电装置的化合物的显示装置。
技术解决方案
在本发明的一个实施例中,提供由以下化学式1表示的化合物。
[化学式1]
在化学式1中,
X1至X10独立地为N、C或CRa,
X1至X10中的至少一者为N,
Z为N-L4-Rb、O、或S,
L1至L4独立地为单键、经取代或未经取代的C1至C30亚烷基、经取代或未经取代的C3至C30环亚烷基、经取代或未经取代的C6至C30亚芳基、经取代或未经取代的C2至C30杂环基、经取代或未经取代的C6至C30亚芳胺基、经取代或未经取代的C1至C30亚烷氧基(alkoxylene group)、经取代或未经取代的C1至C30亚芳氧基(aryloxylene group)、经取代或未经取代的C2至C30亚烯基、经取代或未经取代的C2至C30亚炔基或其组合,
R1至R3以及Ra至Rf独立地为氢、氘、经取代或未经取代的C1至C30烷基、经取代或未经取代的C3至C30环烷基、经取代或未经取代的C2至C30杂环基、经取代或未经取代的C6至C30芳基、经取代或未经取代的胺基、经取代或未经取代的C6至C30芳胺基、经取代或未经取代的C1至C30烷氧基、经取代或未经取代的C2至C30烷氧羰基、经取代或未经取代的C2至C30烷氧基羰基氨基(alkoxycarbonylamino group)、经取代或未经取代的C7至C30芳氧基羰基氨基(aryloxycarbonylamino group)、经取代或未经取代的C1至C30胺磺酰基氨基(sulfamoylamino group)、经取代或未经取代的C2至C30烯基、经取代或未经取代的C2至C30炔基、经取代或未经取代的C3至C40硅烷基、经取代或未经取代的C3至C40硅烷氧基(silyloxy group)、经取代或未经取代的C1至C30酰基、经取代或未经取代的C1至C20酰氧基、经取代或未经取代的C1至C20酰氨基(acylamino group)、经取代或未经取代的C1至C30磺酰基、经取代或未经取代的C1至C30烷基硫醇基、经取代或未经取代的C6至C30芳基硫醇基、经取代或未经取代的C1至C30酰脲基(ureide group)、经取代或未经取代的C5至C40稠环、卤素、氰基、羟基、氨基、硝基、羧基、二茂铁基或其组合,以及
R1至R3独立地存在,或R1至R3的相邻基团彼此稠合以得到环。
根据本发明的一个实施例的化合物可用于有机光电装置。
在本发明的另一实施例中,有机光电装置包含彼此面对的阳极及阴极以及位于阳极与阴极之间的至少一个有机层,其中所述有机层包含所述化合物。
在本发明的又另一实施例中,提供包含所述有机光电装置的显示装置。
有益效果
可实现具有高效率及长使用寿命的有机光电装置。
附图说明
图1及图2为展示根据各种实施例的有机发光二极管的截面视图。
具体实施方式
在下文中,详细描述本发明的实施例。然而,这些实施例为例示性的,且本发明不限于这些实施例。
如本文所用,当不另外提供定义时,术语“经取代”是指经选自氘、卤素、羟基、氨基(amino group)、经取代或未经取代的C1至C30胺基、硝基、经取代或未经取代的C1至C40硅烷基、C1至C30烷基、C1至C10烷基硅烷基、C3至C30环烷基、C6至C30芳基、C1至C20烷氧基、氟基、C1至C10三氟烷基(诸如三氟甲基及其类似基团)或氰基的取代基取代而代替取代基或化合物的至少一个氢。
在本说明书中,当不另外提供特定定义时,“杂”是指在一个官能基中包含1至3个选自N、O、S、P以及Si的杂原子,且其余为碳。
在本说明书中,当不另外提供定义时,“烷基(alkyl)”是指脂族烃基。烷基可为无任何双键或三键的“饱和烷基(saturated alkyl)”。
烷基可为C1至C20烷基。更特定言之,烷基可为C1至C10烷基或C1至C6烷基。举例而言,C1至C4烷基可在烷基链中具有1至4个碳原子,其可选自甲基、乙基、丙基、异丙基、正丁基、异丁基、第二丁基以及第三丁基。
烷基的特定实例可为甲基、乙基、丙基、异丙基、丁基、异丁基、第三丁基、戊基、己基、环丙基、环丁基、环戊基、环己基以及其类似基团。
如本文所用,术语“芳基(aryl)”是指包含具有形成共轭的p-轨域的环的全部元素的取代基,且可为单环或稠环多环(也即共用相邻碳原子对的环)官能基。
如本文所用,术语“杂环基”可指代在一个官能基中包含1至3个选自N、O、S、P以及Si的杂原子且其余为碳的芳基或环烷基。具体言之,当芳基包含杂原子时,其可称为“杂芳基”。
当杂环基为稠环时,杂环基的全部环或每一环可包含杂原子。
更特定言之,经取代或未经取代的C6至C30芳基和/或经取代或未经取代的C2至C30杂芳基可为经取代或未经取代的苯基、经取代或未经取代的萘基、经取代或未经取代的蒽基、经取代或未经取代的亚菲基(phenanthrylene group)、经取代或未经取代的稠四苯基(naphthacenyl group)、经取代或未经取代的芘基(pyrenyl group)、经取代或未经取代的联苯基、经取代或未经取代的对联三苯基(p-terphenyl group)、经取代或未经取代的间联三苯基、经取代或未经取代的屈基(chrysenyl group)、经取代或未经取代的联亚三苯基(triphenylenyl group)、经取代或未经取代的苝基(perylenyl group)、经取代或未经取代的茚基(indenyl group)、经取代或未经取代的呋喃基、经取代或未经取代的噻吩基、经取代或未经取代的吡咯基、经取代或未经取代的吡唑基、经取代或未经取代的咪唑基、经取代或未经取代的三唑基、经取代或未经取代的恶唑基、经取代或未经取代的噻唑基、经取代或未经取代的恶二唑基、经取代或未经取代的噻二唑基(thiadiazolyl group)、经取代或未经取代的吡啶基、经取代或未经取代的嘧啶基、经取代或未经取代的吡嗪基(pyrazinylgroup)、经取代或未经取代的三嗪基(triazinyl group)、经取代或未经取代的苯并呋喃基(benzofuranyl group)、经取代或未经取代的苯并噻吩基(benzothiophenyl group)、经取代或未经取代的苯并咪唑基(benzimidazolyl group)、经取代或未经取代的吲哚基(indolyl group)、经取代或未经取代的喹啉基(quinolinyl group)、经取代或未经取代的异喹啉基(isoquinolinyl group)、经取代或未经取代的喹唑啉基(quinazolinyl group)、经取代或未经取代的喹恶啉基(quinoxalinyl group)、经取代或未经取代的萘啶基(naphthyridinyl group)、经取代或未经取代的苯并恶嗪基(benzoxazinyl group)、经取代或未经取代的苯并噻嗪基(benzthiazinyl group)、经取代或未经取代的吖啶基(acridinylgroup)、经取代或未经取代的啡嗪基(phenazinyl group)、经取代或未经取代的啡噻嗪基(phenothiazinyl group)、经取代或未经取代的啡恶嗪基(phenoxazinylgroup)、经取代或未经取代的茀基(fluorenyl group)、经取代或未经取代的咔唑基、经取代或未经取代的二苯并呋喃基、经取代或未经取代的二苯并噻吩基(dibenzothiophenylgroup)或其组合,但不限于这些基团。
在本说明书中,单键指示直接连接键而不经由碳或除碳以外的杂原子,且特定言之,当L为单键时,连接至L的取代基直接连接至核心。换言之,单键在本说明书中不指示亚甲基及经由碳的类似基团。
在本说明书中,空穴特征是指当施加电场(electric field)时能够供给电子以形成空穴的特征,及由于根据HOMO能阶的导电特征,在阳极中形成的空穴易于注入发射层中且在发射层中传输的特征。
另外,电子特征是指当施加电场时能够接受电子以形成空穴的特征,及由于根据LUMO能阶的导电特征,在阴极中形成的电子易于注入发射层中且在发射层中传输的特征。
在下文中,描述根据一个实施例的化合物。
在本发明的一个实施例中,提供由以下化学式1表示的化合物。
[化学式1]
在化学式1中,
X1至X10独立地为N、C或CRa,
X1至X10中的至少一者为N,
Z为N-L4-Rb、O、或S,
L1至L4独立地为单键、经取代或未经取代的C1至C30亚烷基、经取代或未经取代的C3至C30环亚烷基、经取代或未经取代的C6至C30亚芳基、经取代或未经取代的C3至C30杂环基、经取代或未经取代的C6至C30亚芳胺基、经取代或未经取代的C1至C30亚烷氧基、经取代或未经取代的C1至C30亚芳氧基、经取代或未经取代的C2至C30亚烯基、经取代或未经取代的C2至C30亚炔基或其组合,
R1至R3以及Ra至Rf独立地为氢、氘、经取代或未经取代的C1至C30烷基、经取代或未经取代的C3至C30环烷基、经取代或未经取代的C3至C30杂环基、经取代或未经取代的C6至C30芳基、经取代或未经取代的胺基、经取代或未经取代的C6至C30芳胺基、经取代或未经取代的C1至C30烷氧基、经取代或未经取代的C2至C30烷氧羰基、经取代或未经取代的C2至C30烷氧基羰基氨基、经取代或未经取代的C7至C30芳氧基羰基氨基、经取代或未经取代的C1至C30胺磺酰基氨基、经取代或未经取代的C2至C30烯基、经取代或未经取代的C2至C30炔基、经取代或未经取代的C3至C40硅烷基、经取代或未经取代的C3至C40硅烷氧基、经取代或未经取代的C1至C30酰基、经取代或未经取代的C1至C20酰氧基、经取代或未经取代的C1至C20酰氨基、经取代或未经取代的C1至C30磺酰基、经取代或未经取代的C1至C30烷基硫醇基、经取代或未经取代的C6至C30芳基硫醇基、经取代或未经取代的C1至C30酰脲基、经取代或未经取代的C5至C40稠环、卤素、氰基、羟基、氨基、硝基、羧基、二茂铁基或其组合,以及
R1至R3独立地存在,或R1至R3的相邻基团彼此稠合以得到环。
根据本发明的一个实施例的化合物具有吖啶衍生物与6元环稠合的结构,且因此可调整分子内部空穴及电子的流动,且通过使用所述化合物制造的有机光电装置可在低电压下操作以及具有高效率及长使用寿命。
详言之,所述化合物具有极好的电荷传输且与掺杂剂的吸收光谱充分重迭(overlap),且因此可使诸如高效率、长使用寿命以及在低电压下操作的特征最大化。
特定言之,X2至X10中的至少一者可为N。
化学式1可例如由以下化学式2至化学式14中的一者表示。
在化学式2至化学式14中,X1至X10为C或CRa,
Z为N-L4-Rb,L1至L4、R1至R3、Ra以及Rb与上文所述相同。
当X1至X10中的至少两者为N时,空穴及电子变得较平衡且因此,通过使用由以上化学式2至化学式5表示的每一化合物制造的有机光电装置尤其在效率及驱动电压方面展示极好的特征。
化学式1可例如由以下化学式15至化学式27中的一者表示,但不限于这些化学式。
在化学式15至化学式27中,
Z为N-L4-Rb,
L1及L4独立地为单键、经取代或未经取代的C6至C30亚芳基、经取代或未经取代的C2至C30杂环基或其组合,以及
R1及Rb独立地为氢、氘、经取代或未经取代的C1至C30烷基、经取代或未经取代的C2至C30杂环基、经取代或未经取代的C6至C30芳基、经取代或未经取代的C5至C40稠环或其组合。
L1及L4独立地为单键或选自以下群组I中列出的经取代或未经取代的基团的基团,但不限于此。
[群组1]
在群组I中,*指示连接点。
R1及Rb独立地为氢、氘或选自以下群组II中列出的经取代或未经取代的基团的基团,但不限于此。
[群组II]
在群组II中,
R及R'独立地为氢、氘、经取代或未经取代的C1至C30烷基、经取代或未经取代的C6至C30芳基、经取代或未经取代的C2至C30杂芳基或其组合,且*为连接点。
化学式1的Z可为N-L4-Rb,其中Rb为氢、氘、经取代或未经取代的C2至C30杂环基、经取代或未经取代的C6至C30芳基、经取代或未经取代的C5至C40稠环或其组合。
所述化合物可为例如以下群组III中列出的化合物,但不限于这些化合物。
[群组III]
所述化合物可用于有机光电装置。
在下文中,描述应用所述化合物的有机光电装置。
在本发明的另一实施例中,有机光电装置包含彼此面对的阳极及阴极以及插入于阳极与阴极之间的至少一个有机层,其中所述有机层包含所述化合物。
有机层可包含发射层,且发射层可包含本发明的化合物。
特定言之,可包含所述化合物作为发射层的主体。
另外,在本发明的一个实施例中,有机层包含至少一个选自空穴注入层、空穴传输层、电子阻挡层、电子传输层、电子注入层以及空穴阻挡层的辅助层,其中所述辅助层可包含所述化合物。
有机光电装置可为将电能转换成光能且将光能转换成电能而无特别限制的任何装置,且可为例如有机光电装置、有机发光二极管、有机太阳能电池以及有机感光鼓。
在本文中,参照附图描述作为有机光电装置的一个实例的有机发光二极管。
图1及图2为根据一个实施例的各有机发光二极管的截面视图。
参照图1,根据一个实施例的有机发光二极管100包含彼此面对的阳极120及阴极110以及插入于阳极120与阴极110之间的有机层105。
阳极120可由具有大功函数的导体制成以有助于空穴注入,且可为例如金属、金属氧化物和/或导电聚合物。阳极120可为例如金属镍、铂、钒、铬、铜、锌、金以及其类似物或其合金;金属氧化物,诸如氧化锌、氧化铟、氧化铟锡(indium tin oxide;ITO)、氧化铟锌(indium zinc oxide;IZO)以及其类似物;金属及氧化物的组合,诸如ZnO及Al或SnO2及Sb;导电聚合物,诸如聚(3-甲基噻吩)、聚(3,4-(亚乙基-1,2-二氧基)噻吩)(poly(3,4-(ethylene-1,2-dioxy)thiophene);PEDT)、聚吡咯以及聚苯胺,但不限于此。
阴极110可由具有小功函数的导体制成以有助于电子注入,且可为例如金属、金属氧化物和/或导电聚合物。阴极110可为例如金属或其合金,诸如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡、铅、铯、钡以及其类似物;多层结构材料,诸如LiF/Al、LiO2/Al、LiF/Ca、LiF/Al以及BaF2/Ca,但不限于此。
有机层105包含包括所述化合物的发射层130。
发射层130可包含例如仅所述化合物、至少两种类型的所述化合物的混合物或所述化合物与另一化合物的混合物。当使用所述化合物与另一化合物的混合物时,例如可包含所述化合物与另一化合物作为主体(host)及掺杂剂(dopant),且所述化合物可充当例如主体。主体可为例如磷光主体或荧光主体,且例如磷光主体。
当所述化合物用作主体时,掺杂剂可选自无机、有机、有机/无机化合物,且可选自熟知掺杂剂。
参照图2,有机发光二极管200还包含空穴辅助层140以及发射层230。空穴辅助层140增加阳极120与发射层230之间的空穴注入和/或空穴迁移率,且阻断电子。空穴辅助层140可为例如空穴传输层(hole transport layer;HTL)、空穴注入层(hole injectionlayer;HIL)和/或电子阻挡层,且可包含至少一个层。所述化合物可包含在发射层230和/或空穴辅助层140中。
尽管图1或图2中未展示,但有机层105可还包含电子注入层(electron injectionlayer;EIL)、电子传输层(electron transport layer;ETL)、辅助空穴传输层(HTL)、空穴注入层(HIL)或其组合。本发明的化合物可包含在这些有机层中。有机发光二极管100,200可通过在基板上形成阳极或阴极,根据干式涂布法(诸如蒸发(evaporation)、溅镀(sputtering)、电浆电镀以及离子电镀)或湿式涂布法(诸如旋涂(spin coating)、浸渍(dipping)、淋涂(flow coating))形成有机层,以及在上面形成阴极或阳极来制造。
有机发光二极管可应用于有机发光二极管(OLED)显示器。
发明模式
在下文中,参照实例更详细地说明实施例。然而,这些实例在任何意义上均不解释为限制本发明的范畴。
(化合物的制备)
实例1:化合物B-17的合成
作为根据本发明的化合物的特定实例的化合物B-17经由以下四个步骤来合成。
[反应流程1]
第一步:合成中间产物(L-1)
将39.0克(195.9毫摩尔)2,4-二氯喹唑啉、53.7克(215.5毫摩尔)4,4,5,5-四甲基-2-(2-硝基苯基)1,3,2-二氧杂硼戊烷(4,4,5,5-tetramethyl-2-(2-nitrophenyl)-l,3,2-dioxaborolane)、67.7克(489.9毫摩尔)碳酸钾以及11.3克(9.8毫摩尔)四(三苯基膦)钯添加至2000毫升烧瓶中的650毫升1,4-二恶烷及300毫升水中,且随后在氮气流下,在60℃下加热混合物12小时。将所获得的混合物添加至2000毫升甲醇中,将其中结晶的固体过滤且随后溶解于单氯苯中并用硅胶/硅藻土再次过滤,且在自其中移除适量有机溶剂后,使用甲醇进行再结晶,获得中间物L-1(29.1克,51%的产率)。
C14H8ClN3O2的计算值:C,58.86;H,2.82;Cl,12.41;N,14.71;O,11.20;实验值:C,58.30;H,2.92;Cl,12.13;N,14.21;O,10.82
第二步:合成中间产物(L-2)
将29.0克(101.5毫摩尔)中间物L-1、14.2克(116.73毫摩尔)苯硼酸、35.1克(253.7毫摩尔)碳酸钾以及5.9克(5.1毫摩尔)四(三苯基膦)钯添加至1000毫升烧瓶中的350毫升1,4-二恶烷及150毫升水,且随后在氮气流下,在60℃下加热混合物12小时。将所获得的混合物添加至1000毫升甲醇中,将其中结晶的固体过滤、溶解于单氯苯中且用硅胶/硅藻土再次过滤,且随后在自其中移除适量有机溶剂后,使用甲醇进行再结晶,获得中间物L-2(23.6克,71%的产率)。
C20H13N3O2的计算值:C,73.38;H,4.00;N,12.84;O,9.78;实验值:C,72.99;H,3.96;N,12.81;O,9.77
第三步:合成中间产物(L-3)
将26.0克(79.43毫摩尔)中间物L-2添加至500毫升烧瓶中的200毫升亚磷酸三乙酯中,且在氮气流下,在170℃下加热混合物12小时。所获得的混合物经分馏以移除溶剂且随后经由管柱层析处理,获得中间物L-3(14.1克,60.0%的产率)。
C20H13N3的计算值:C,81.34;H,4.44;N,14.23;实验值:C,81.12;H,4.39;N,14.16
第四步:合成化合物B-17
将8.4克(28.5毫摩尔)中间物L-3、8.0克(29.97毫摩尔)1-氯-3,5-二苯基嘧啶、5.5克(57.1毫摩尔)第三丁醇钠、0.6克(2.9毫摩尔)三(二苯亚甲基丙酮)二钯(0)、2.3毫升三第三丁基膦(50%于甲苯中)添加至500毫升圆形烧瓶的200毫升二甲苯中,且在氮气流下加热混合物并回流15小时。接着,将500毫升甲醇添加至所获得的混合物,将其中结晶的固体过滤,溶解于二氯苯中且用硅胶/硅藻土过滤,并使用甲醇进行再结晶以移除适量有机溶剂,获得化合物B-17(10.0克,67%的产率)。
C36H23N5的计算值:C,82.26;H,4.41;N,13.32;实验值:C,82.25;H,4.34;N,13.02
实例2:化合物B-33的合成
作为根据本发明的化合物的特定实例的化合物B-33经由以下一个步骤来合成。
第一步:合成化合物B-33
将8.3克(28.3毫摩尔)中间物L-3、11.5克(29.7毫摩尔)2-(3-溴苯基)-4,6-二苯基嘧啶、5.4克(56.5毫摩尔)第三丁醇钠、0.6克(2.8毫摩尔)三(二苯亚甲基丙酮)二钯(0)以及2.3毫升三第三丁基膦(50%于甲苯中)添加至500毫升圆形烧瓶中的200毫升二甲苯中,且在氮气流下加热混合物并回流15小时。将所获得的混合物添加至500毫升甲醇中,将其中结晶的固体过滤,溶解于二氯苯中且用硅胶/硅藻土过滤,且在自其中移除适量有机溶剂后,使用甲醇进行再结晶,获得化合物B-33(11.2克,66%的产率)。
C42H27N5的计算值:C,83.84;H,4.52;N,11.64;实验值:C,83.57;H,4.44;N,11.51
实例3:化合物A-105的合成
作为根据本发明的化合物的特定实例的化合物A-105经由以下一个步骤来合成。
第一步:合成化合物A-105
将8.3克(28.0毫摩尔)中间物L-3、10.8克(29.4毫摩尔)9-苯基-3-溴-咔唑、5.4克(56.0毫摩尔)第三丁醇钠、1.6克(2.8毫摩尔)三(二苯亚甲基丙酮)二钯(0)以及2.3毫升三第三丁基膦(50%于甲苯中)添加至500毫升圆形烧瓶中的190毫升二甲苯中,且在氮气流下加热混合物并回流15小时。将所获得的混合物添加至500毫升甲醇中,将其中结晶的固体过滤,溶解于二氯苯中且用硅胶/硅藻土过滤,且随后在自其中移除适量有机溶剂后,使用甲醇进行再结晶,获得化合物A-105(9.5克,63%的产率)。
C38H24N4的计算值:C,85.05;H,4.51;N,10.44;实验值:C,85.01;H,4.47;N,10.32
比较例1:CBP的合成
以与国际公开案WO 2013032035中所揭示相同的方法合成由以下化学式a表示的化合物。
化学式a
(所制备化合物的模拟特征比较)
通过使用超级电脑GAIA(IBM power 6)以高斯09方法(Gaussian 09 method)计算各材料的能阶,且结果提供于下表1中。
[表1]
化合物 | 偶极矩 | HOMO(eV) | LUMO(eV) | T1(eV) | S1(eV) |
比较例1 | 0.0829 | -5.319 | -1.231 | 2.971 | 3.560 |
实例1 | 8.3085 | -5.075 | -2.198 | 2.302 | 3.145 |
实例2 | 8.2130 | -5.082 | -1.904 | 2.324 | 3.167 |
实例3 | 8.1971 | -5.052 | -1.476 | 2.321 | 3.203 |
如表1中所示,由于模拟中所需HOMO/LUMO能阶(HOMO为-5.0至-5.5且LUMO为-1.4至-2.2)充分展示电子传输特征,比较例1满足HOMO能阶但未满足LUMO能阶,且因此与实例1、实例2以及实例3相比,展示空穴与电子之间的不平衡。
本发明的化合物与比较例1相比具有适当能阶,且因此预期展示极好的效率及使用寿命。
(有机发光二极管的制造)
实例4
通过使用实例1的化合物B-17作为主体及(piq)2Ir(acac)作为掺杂剂来制造有机发光二极管。
使用1000埃厚的ITO作为阳极,且使用1000埃厚的铝(Al)作为阴极。特定言之,说明一种制造有机发光二极管的方法,阳极是通过将具有15欧姆/平方厘米薄层电阻的ITO玻璃基板切割成50毫米×50毫米×0.7毫米的尺寸,将其分别在丙酮、异丙醇以及纯水中超音波清洁15分钟且将其紫外线臭氧清洁30分钟来制造。
在基板上,通过在650×10-7帕真空度下以0.1至0.3纳米/秒的沉积速率沉积N4,N4'-二(萘-1-基)-N4,N4'-二苯基联苯-4,4'-二胺(N4,N4'-di(naphthalene-l-yl)-N4,N4'-diphenylbiphenyl-4,4'-diamine,NPB)(80纳米)形成800埃厚的空穴传输层(HTL)。随后,通过在相同真空沉积条件下使用实例1的化合物B-17形成300埃厚的发射层,且在本文中,同时沉积磷光掺杂剂(piq)2Ir(acac)。在本文中,以发射层总重量的100重量%计,通过调节沉积速率沉积3重量%磷光掺杂剂。
在发射层上,通过在相同真空沉积条件下沉积双(2-甲基-8-喹啉)-4-(苯基苯酚)铝(bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium,BAlq)形成50埃厚的空穴阻挡层。随后,通过在相同真空沉积条件下沉积Alq3形成200埃厚的电子传输层(ETL)。在电子传输层(ETL)上,通过依次沉积LiF及Al形成阴极,从而制造有机光电装置。
有机光电装置的结构为ITO/NPB(80纳米)/EML(B-17(97重量%)+(piq)2Ir(acac)(3重量%),30纳米)/Balq(5纳米)/Alq3 20(纳米)/LiF(1纳米)/Al(100纳米)。
实例5
除使用实例2的化合物B-33代替实例4的化合物B-17以外,根据与实例4相同的方法制造有机发光二极管。
实例6
除使用实例3的化合物A-105代替实例4的化合物B-17以外,根据与实例4相同的方法制造有机发光二极管。
比较例2
除使用以下结构的CBP代替实例4的化合物B-17以外,根据与实例4相同的方法制造有机发光二极管。
用于制造有机发光二极管的NPB、BAlq、CBP以及(piq)2Ir(acac)的结构如下。
(有机发光二极管的效能量测)
量测根据实例4、实例5、实例6以及比较例2的各有机发光二极管视电压及发光效率而定的电流密度及亮度变化。
特定言之,在以下方法中进行量测,且结果提供于下表2中。
(1)量测视电压变化而定的电流密度变化
使用电流-电压计(吉时利2400(Keithley 2400))在使电压自0伏增加至10伏的同时,量测所制造的有机发光二极管的单元装置中流动的电流值,且所量测的电流值除以面积,得出结果。
(2)量测视电压变化而定的亮度变化
使用亮度计(美能达Cs-1000A(Minolta Cs-1000A))在使电压自0伏增加至10伏的同时,关于亮度量测所制造的有机发光二极管的亮度。
(3)量测发光效率
通过使用项目(1)及(2)的亮度、电流密度以及电压(伏)计算在相同电流密度(10毫安/平方厘米)下的电流效率(cd/A)。
(4)量测使用寿命
通过在亮度(cd/m2)保持在5000cd/m2的同时量测直至电流效率(cd/A)降至90%消耗的时间来获得使用寿命。
[表2]
参照表2,根据实例4至实例6的绿色有机发光二极管与比较例2相比,展示明显改良的驱动电压、发光效率和/或功率效率。
尽管已结合目前视为实用例示性实施例的内容来描述本发明,但应理解本发明不限于所揭示的实施例,而相反地,本发明意欲涵盖包含在所附权利要求书的精神及范畴内的各种修改及等效配置。因此,上述实施例应理解为例示性的但不以任何方式限制本发明。
Claims (8)
3.根据权利要求1或2所述的由化学式15表示的化合物,其中所述化合物用于有机光电装置。
4.一种有机光电装置,其特征在于,包括
彼此面对的阳极及阴极,以及
至少一个位于所述阳极与所述阴极之间的有机层,
其中,所述有机层包括如权利要求1至3中任一项所述的由化学式15表示的化合物。
5.根据权利要求4所述的有机光电装置,其中所述有机层包括发射层,
其中所述发射层包括所述化合物。
6.根据权利要求5所述的有机光电装置,其中包含所述化合物作为所述发射层的主体。
7.根据权利要求4所述的有机光电装置,其中所述有机层包括至少一个选自空穴注入层、空穴传输层、电子阻挡层、电子传输层、电子注入层以及空穴阻挡层的辅助层,
其中所述辅助层包括所述化合物。
8.一种显示装置,其特征在于,包括如权利要求4所述的有机光电装置。
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