CN114975839A - 一种有机电致发光器件、有机电致发光装置及光电设备 - Google Patents
一种有机电致发光器件、有机电致发光装置及光电设备 Download PDFInfo
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- CN114975839A CN114975839A CN202210885193.8A CN202210885193A CN114975839A CN 114975839 A CN114975839 A CN 114975839A CN 202210885193 A CN202210885193 A CN 202210885193A CN 114975839 A CN114975839 A CN 114975839A
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- organic electroluminescent
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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Abstract
本发明涉及一种有机电致发光器件、有机电致发光装置及光电设备,属于有机电致发光装置技术领域,有机电致发光器件包括第一电极、面向所述第一电极的第二电极、在所述第一电极与所述第二电极之间的发光层、以及在所述第一电极与所述发光层之间的空穴传输区域;所述空穴传输区域包括空穴注入层,第一空穴传输层,第二空穴传输层。本发明提供了一种在空穴传输区域中包含具有特定的芳基胺衍生物以及在发光层中包含双主体红光材料的特定组合制备成的有机电致发光器件,制备的有机电致发光器件具有高启亮电压的同时,具有较低驱动电压,并保留了双主体红光器件高效率长寿命的器件优势,通过提高红光器件的启亮电压缓解串扰所带来的显色偏红现象。
Description
技术领域
本发明涉及有机电致发光装置技术领域,具体是一种有机电致发光器件、有机电致发光装置及光电设备。
背景技术
有机电致发光显示器(OLED)是主动发光显示装置。目前中小尺寸的OLED显示屏已经在华为、小米、三星等公司出品的高端智能手机上得到了大规模的应用,在低工作电压条件下获得器件的最佳发光效率是OLED领域的普遍需求。降低驱动电压是降低功耗、提高器件发光效率及稳定性等问题的一种重要途径。目前较多方法用来实现器件的低压驱动进而提高器件发光效率,其中之一是采用激基复合物主体材料(exciplex-forming cohost),即双主体材料。通常由空穴传输型主体材料(P型)和电子传输型主体材料(N型)组成,罗门哈斯等公司推出一系列产品,已经应用到产线,实现了低驱动电压、高效率、长寿命的效果。
启亮电压定义为器件发光亮度达到1nits时所需要施加的电压。在现有的OLED显示器件中,RGB三色子像素的启亮电压是不一致的。具体为,蓝光子像素的启亮电压大于绿光子像素的启亮电压大于红光子像素的启亮电压。实际应用时,由于蓝光子像素在不同的驱动电压条件下存在较大的效率差异。在低电压驱动下,蓝光子像素发光效率较低。然而,红光子像素、绿光子像素的驱动电压相对较低,在低电压驱动下能够正常发光,这就使得,在低灰阶情况下,红光子像素发光效率高于绿光子像素和蓝光子像素的发光效率,屏体出现显色偏红现象,发生串扰现象。
提高红光器件的启亮电压缓解串扰所带来的显色偏红现象,单主体红光器件的启亮电压虽然比双主体红光器件的启亮电压高,但存在发光效率低和寿命短的问题,而双主体红光器件的启亮电压的提高通常会伴随着驱动电压的升高。
发明内容
本发明的目的在于提供一种有机电致发光器件、有机电致发光装置及光电设备,以解决上述背景技术中提出的问题。
为实现上述目的,本发明提供如下技术方案:
一种有机电致发光器件,包括第一电极、面向所述第一电极的第二电极、在所述第一电极与所述第二电极之间的发光层、以及在所述第一电极与所述发光层之间的空穴传输区域;所述空穴传输区域包括空穴注入层,第一空穴传输层,第二空穴传输层;
所述第二空穴传输层的结构通式如式I所示:
其中,
Ar’1,Ar’2各自独立地为取代或未取代的C6-C24芳基、取代或未取代的3元至24元杂芳基;
R’1-R’3各自独立地为氢、氘、取代或未取代的C1-C6烷基、取代或未取代的C6-C18芳基、取代或未取代的3元至18元杂芳基、取代或未取代的C3-C12环烷基、取代或未取代的C1-C6烷氧基;
R’4为氢,甲基,乙基,苯基或联苯基;
R’1-R’4与所在苯环以取代或形成稠合环的方式连接;
所述发光层包含P型主体材料和N型主体材料;
所述P型主体材料的结构通式如式II所示:
其中,
Y1,Y2选自如下组合:
Y1为N,Y2为O;
Y1为N,Y2为S;
Y1为O,Y2为N;
Y1为S,Y2为N;
L1为连接键、取代或未取代的C6-C18亚芳基、取代或未取代的3元至18元亚杂芳基;
Ar1-Ar3各自独立地为取代或未取代的C6-C24芳基、取代或未取代的3元至24元杂芳基;
Ar1-Ar3与所在苯环以取代或形成稠合环的方式连接;
所述N型主体材料的结构通式如式III所示:
其中,
X1选自O或S;
m,n,p中一个为1,其余为0;
Z1-Z3各自独立地为N或C,且至少一个为N;
Ar4-Ar5各自独立地为取代或未取代的C6-C24芳基、取代或未取代的3元至24元杂芳基;
L2为连接键、取代或未取代的C6-C18亚芳基、取代或未取代的3元至18元亚杂芳基。
作为本发明的进一步技术方案,所述第二空穴传输层选自如下式I-1至式I-3中的一种:
其中,
R’1-R’2各自独立地为氢、氘、甲基、乙基、异丙基、丙基、叔丁基、苯基、萘基、联苯基、吡啶基、甲氧基、菲基、二苯并呋喃基或二甲基芴基;
R’3为氘、甲基、乙基、丙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、甲氧基、菲基、二甲基芴基或呋喃基;
Ar’1与Ar’2在任意可取代位置与N进行连接;
Ar’1,Ar’2各自独立的为如下基团中的一种或如下基团的组合:
作为本发明的更进一步技术方案,所述第二空穴传输层选自如下HT-1至HT-56中的一种:
作为本发明的再进一步技术方案,所述P型主体材料选自如下式II-a至式II-d中的一种:
其中,
L1为连接键、苯基、萘基、联苯基、三联苯基、吡啶基、菲基、二苯并呋喃基、二苯并噻吩基或二甲基芴基;
Ar1-Ar3各自独立地为自苯基、甲基苯基、乙基苯基、异丙基苯基、叔丁基苯基、萘基、联苯基、三联苯基、吡啶基、菲基、二苯并呋喃基、二苯并噻吩基、二甲基芴基或咔唑基。
作为本发明的再进一步技术方案,所述P型主体材料选自如下式RH1-1至RH1-85中的一种:
作为本发明的再进一步技术方案,所述N型主体材料选自如下式III-a至式III-c中的一种:
其中,
L2为连接键、苯基、萘基、联苯基、吡啶基、菲基、二苯并呋喃基、二苯并噻吩基或二甲基芴基;
Ar4-Ar5各自独立地为苯基、甲基苯基、乙基苯基、异丙基苯基、叔丁基苯基、萘基、联苯基、三联苯基、吡啶基、菲基、二苯并呋喃基、二苯并噻吩基、二甲基芴基或咔唑基。
作为本发明的再进一步技术方案,所述N型主体材料选自如下RH2-1至RH2-96中的一种:
与现有技术相比,本发明的有益效果是:提供了一种在空穴传输区域中包含具有特定的芳基胺衍生物以及在发光层中包含双主体红光材料的特定组合制备成的有机电致发光器件,制备的有机电致发光器件具有高启亮电压的同时,具有较低驱动电压,并保留了双主体红光器件高效率长寿命的器件优势,通过提高红光器件的启亮电压缓解串扰所带来的显色偏红现象。
在本说明书中,术语“经取代或未取代的”意指被选自以下的一个、两个或更多个取代基取代:氘;卤素基团;腈基;甲硅烷基;硼基;C1-C6的烷基;C3-C10环烷基;C6-C18的芳基;C3-C30的杂环基,或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代,或者不具有取代基。
附图说明
图1为应用例4和对比例2制备的有机电致发光器件的启亮电压图。
具体实施方式
一种有机电致发光器件,包括第一电极、面向所述第一电极的第二电极、在所述第一电极与所述第二电极之间的发光层、以及在所述第一电极与所述发光层之间的空穴传输区域;其特征在于,所述空穴传输区域包括空穴注入层,第一空穴传输层,第二空穴传输层;
所述第二空穴传输层的结构通式如式I所示:
具体选自如下HT-1至HT-56中的一种:
所述发光层包含P型主体材料和N型主体材料;
所述P型主体材料的结构通式如式II所示:
具体为选自如下式RH1-1至RH1-85中的一种:
所述N型主体材料的结构通式如式III所示,
具体为选自如下RH2-1至RH2-96中的一种:
上述有机电致发光器件中第二空穴传输层的合成路线如下:
N2保护下,在反应容器中将反应物A(1.0eq)、反应物B(1.0-1.3eq)、四(三苯基膦)钯(0.01-0.05eq)和碳酸钾(2.0-2.5eq)分别加入到甲苯、乙醇、水(V甲苯:V乙醇:V水=2-4:1:1)的混合溶剂中,升温至90-110℃,反应6-10h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到式I。
Hal1为Cl,Br,I。
上述有机电致发光器件中P型主体材料的合成路线如下:
当L1不为连接键时:
N2保护下,在反应容器中将反应物C(1.0eq)、反应物D(1.0-1.2eq)、四(三苯基膦)钯(0.01-0.04eq)和碳酸钾(2.0-2.4eq)分别加入到甲苯、乙醇、水(V甲苯:V乙醇:V水=2-4:1:1)的混合溶剂中,升温至90-110℃,反应6-10h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到式II。
当L1为连接键时:
N2保护下,将反应物C(1.0eq)、反应物D(1.0-1.2eq)、Pd(OAc)2(0.01-0.04eq)、P(t-Bu)3(0.05-0.1eq)、NaOtBu(2.0-2.5eq)、以及邻-二甲苯添加到反应容器中并溶解,加热到135-145℃,反应2-4小时。在反应完成后,将有机层用乙酸乙酯萃取,用柱色谱法分离以获得式II。
Hal2为Cl,Br,I。
上述有机电致发光器件中N型主体材料的合成路线如下:
N2保护下,在反应容器中将反应物E(1.0eq)、反应物F(1.0-1.2eq)、四(三苯基膦)钯(0.01-0.04eq)和碳酸钾(2.0-2.4eq)分别加入到甲苯、乙醇、水(V甲苯:V乙醇:V水=2-4:1:1)的混合溶剂中,升温至90-110℃,反应6-10h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到式III。
Hal3为Cl,Br,I。
实施例1:第二空穴传输层HT-13的合成:
CAS:HT-13-B:55135-66-5
N2保护下,在反应容器中将反应物HT-13-A(40mmol)、反应物HT-13-B(48mmol)、四(三苯基膦)钯(0.04mmol)和碳酸钾(88mmol)分别加入到甲苯(90mL)、乙醇(30mL)、水(30mL)的混合溶剂中,升温至100℃,反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到化合物HT-13(24.37g,产率:88%)。
表征:
HPLC纯度:>99.8%;
质谱测试:理论值为691.92;测试值为692.26;
元素分析:
理论值:C, 92.00; H, 5.97; N, 2.02;
测试值:C, 91.70; H, 6.25; N, 2.14。
实施例2:第二空穴传输层HT-24的合成:
CAS:HT-24-A:1959599-90-6
CAS:HT-24-B:55135-66-5
CAS:HT-24:2227490-15-3
N2保护下,在反应容器中将反应物HT-24-A(40mmol)、反应物HT-24-B(48mmol)、四(三苯基膦)钯(0.04mmol)和碳酸钾(88mmol)分别加入到甲苯(90mL)、乙醇(30mL)、水(30mL)的混合溶剂中,升温至100℃,反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到化合物HT-24(24.37g,产率:85%)。
表征:
HPLC纯度:>99.7%;
质谱测试:理论值为677.89;测试值为678.30;
元素分析:
理论值:C, 92.13; H, 5.80; N, 2.07;
测试值:C, 91.93; H, 6.02; N, 2.15。
实施例3:P型主体材料RH1-32的合成:
CAS:RH1-32-C:2085325-16-0
CAS:RH1-32-D:2230816-66-5
N2保护下,将反应物RH1-32-C(40mmol)、反应物RH1-32-D(44mmol)、Pd(OAc)2(0.4mmol)、P(t-Bu)3(2mmol)、NaOtBu(88mmol)、以及邻-二甲苯添加到反应容器中并溶解,加热到140℃,反应4小时。在反应完成后,将有机层用乙酸乙酯萃取,用柱色谱法分离获得化合物RH1-32(19.62g,产率:78%)。
表征:
HPLC纯度:>99.7%;
质谱测试:理论值为628.73;测试值为629.01;
元素分析:
理论值:C, 85.97; H, 4.49; N, 4.46; O, 5.09;
测试值:C, 85.82; H, 4.62; N, 4.52; O, 5.16。
实施例4:P型主体材料RH1-50的合成:
CAS:RH1-50-C:2085325-18-2
CAS:RH1-50-D:2222194-15-0
CAS:RH1-50:2649505-53-1
N2保护下,在反应容器中将反应物RH1-50-C(40mmol)、反应物RH1-50-D(48mmol)、四(三苯基膦)钯(0.6mmol)和碳酸钾(84mmol)分别加入到甲苯(90mL)、乙醇(30mL)、水(30mL)的混合溶剂中,升温至95℃,反应10h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到化合物RH1-50(20.13g,产率:80%)。
表征:
HPLC纯度:>99.8%;
质谱测试:理论值为628.73;测试值为629.01;
元素分析:
理论值:C, 85.97; H, 4.49; N, 4.46; O, 5.09;
测试值:C, 85.82; H, 4.62; N, 4.52; O, 5.16。
实施例5:P型主体材料RH1-57的合成:
N2保护下,在反应容器中将反应物RH1-57-C(40mmol)、反应物RH1-57-D(45mmol)、四(三苯基膦)钯(0.4mmol)和碳酸钾(84mmol)分别加入到甲苯(90mL)、乙醇(30mL)、水(30mL)的混合溶剂中,升温至95℃,反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到化合物RH1-57(22.98g,产率:83%)。
表征:
HPLC纯度:>99.8%;
质谱测试:理论值为691.83;测试值为692.19;
元素分析:
理论值:C, 86.81; H, 4.81; N, 6.07; O, 2.31;
测试值:C, 86.58; H, 4.98; N, 6.12; O, 2.39。
实施例6:N型主体材料RH2-5的合成:
CAS:RH2-5-E:2204284-97-7
CAS:RH2-5-F:1970122-69-0
CAS:RH2-5:2649505-87-1
N2保护下,在反应容器中将反应物RH2-5-E(40mmol)、反应物RH2-5-F(48mmol)、四(三苯基膦)钯(0.4mmol)和碳酸钾(84mmol)分别加入到甲苯(90mL)、乙醇(30mL)、水(30mL)的混合溶剂中,升温至95℃,反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到化合物RH2-5(17.28g,产率:75%)。
表征:
HPLC纯度:>99.7%;
质谱测试:理论值为575.67;测试值为576.13;
元素分析:
理论值:C, 85.54; H, 4.38; N, 7.30; O, 2.78;
测试值:C, 85.29; H, 4.62; N, 7.35; O, 2.84。
实施例7:N型主体材料RH2-29的合成:
CAS:RH2-29:2649507-42-4
N2保护下,在反应容器中将反应物RH2-29-E(40mmol)、反应物RH2-29-F(48mmol)、四(三苯基膦)钯(0.4mmol)和碳酸钾(84mmol)分别加入到甲苯(90mL)、乙醇(30mL)、水(30mL)的混合溶剂中,升温至90℃,反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到化合物RH2-29(18.20g,产率:79%)。
表征:
HPLC纯度:>99.7%;
质谱测试:理论值为575.67;测试值为576.07;
元素分析:
理论值:C, 85.54; H, 4.38; N, 7.30; O, 2.78;
测试值:C, 85.39; H, 4.50; N, 7.36; O, 2.84。
实施例8:N型主体材料RH2-78的合成:
N2保护下,在反应容器中将反应物RH2-78-E(40mmol)、反应物RH2-78-F(48mmol)、四(三苯基膦)钯(0.4mmol)和碳酸钾(84mmol)分别加入到甲苯(90mL)、乙醇(30mL)、水(30mL)的混合溶剂中,升温至95℃,反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤,干燥滤饼;置于1,4-二氧六环中重结晶,得到化合物RH2-78(17.28g,产率:72%)。
表征:
HPLC纯度:>99.8%;
质谱测试:理论值为727.87;测试值为728.23;
元素分析:
理论值:C, 87.46; H, 4.57; N, 5.77; O, 2.20;
测试值:C, 87.72; H, 4.67; N, 5.84; O, 2.27。
本发明通过在空穴传输区域中包含本公开的式I所示的具有特定的芳基胺衍生物以及在发光层中包含本公开式II,式III所示的双主体红光材料特定组合制备成的有机电致发光器件,具有高启亮电压的同时,具有较低驱动电压,并保留了双主体红光器件高效率长寿命的器件优势,用以缓解串扰所带来的显色偏红现象。
本发明所述有机电致发光器件包括第一电极、面向所述第一电极的第二电极、在所述第一电极与所述第二电极之间的发光层、以及在所述第一电极与所述发光层之间的空穴传输区域。
本发明空穴传输区域包括空穴注入层,第一空穴传输层,第二空穴传输层,第二空穴传输层材料也可以作为发光辅助层材料,电子阻挡层材料。
本发明第二空穴传输层材料为式I所示化合物构成。
本发明主体材料为红光双主体材料,由式II,式III所示化合物构成。
本发明的有机电致发光装置,可以为顶部发光型、底部发光型或双向发光型。本发明所述的器件可以用于有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
本发明的有机电致发光装置包括第一电极、面向所述第一电极的第二电极、在所述第一电极与所述第二电极之间的发光层、在所述第一电极与所述发光层之间的空穴传输区域、以及在所述发光层与所述第二电极之间的电子传输区域。第一电极和第二电极之一是阳极,并且另一个是阴极。
有机发光元件可以具有包含空穴注入层、空穴传输层、电子阻挡层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层等作为有机物层的结构。但是,有机发光元件的结构并不限于此,可以包含数量更少或更多的有机层。
有机发光元件可以通过在基板上依次层叠第一电极、有机物层和第二电极制造。可以通过溅射法(sputtering)或电子束蒸发法(ebeam evaporation)之类的物理蒸镀方法(physical Vapor Deposition,PVD) 进行制造。
在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成第一电极,在该第一电极上形成包含空穴注入层、空穴传输层、发光层和电子传输层的有机物层,然后在该有机物层上蒸镀可用作第二电极的物质。除了这样的方法以外,也可以在基板上依次蒸镀第二电极物质、有机物层、第一电极物质来制造有机发光元件。
此外,关于上述化学式I,式II,式III所表示的化合物,在制造有机发光元件时,不仅可以利用真空蒸镀法,也可以利用溶液涂布法来形成有机物层。其中,所谓溶液涂布法是指,旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但并非仅限于此。
本发明第一电极为阳极,第二电极为阴极。
作为阳极物质,通常为了使空穴能够顺利地向有机物层注入,优选为功函数大的物质。作为本发明中可使用的阳极物质的具体例,有钒、铬、铜、锌、金等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO:A1或SnO2:Sb等金属与氧化物的组合;聚吡咯及聚苯胺等导电性高分子等。
作为上述阴极物质,通常为了使电子容易地向有机物层注入,优选为功函数小的物质。作为阴极物质的具体例,有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡及铅等金属或它们的合金:LiF/A1或LiO2/A1,Mg/Ag等多层结构物质等。
空穴传输区域意指其中空穴在第一电极和发光层之间传输的区域。空穴传输区域是接收来自空穴注入层的空穴并将空穴传输至发光层的区域。可以将空穴传输区域放置在阳极(或空穴注入层)与发光层之间。空穴传输区域可以用于平稳地使从阳极转移的空穴移动到发光层,并阻挡从阴极转移的电子以保留在发光层中。
本发明空穴传输区域包括空穴注入层,第一空穴传输层,第二空穴传输层,第二空穴传输层材料也可以作为发光辅助层材料,电子阻挡层材料。
本发明第二空穴传输层材料由式I所示化合物构成;
在本发明中,空穴注入层优选为p掺杂的空穴注入层,p掺杂的空穴注入层意指掺杂有p掺杂剂的空穴注入层。p掺杂剂是能够赋予p型半导体特性的材料。p型半导体特性意指在HOMO能级下注入空穴或传输空穴的特性,即具有高空穴传导率的材料的特性。
可以将第二空穴传输层放置在阳极与发光层之间,或者放置在阴极与发光层之间。当将第二空穴传输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。当将第二空穴传输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。
发光层的发光物质,是能够分别接收来自空穴传输层和电子传输层的空穴和电子并使其结合而发出可见光区域的光的物质,优选为对于荧光或磷光的量子效率高的物质。
发光层可以包含主体材料和掺杂剂材料。
本发明主体材料为红光双主体材料,由式II,式III所示化合物构成;
电子传输区域可以包括电子缓冲层、空穴阻挡层、电子传输层和电子注入层中的至少一个,并且优选电子传输层和电子注入层中的至少一个。电子传输区域是能够改善在制造面板的过程期间当装置暴露于高温时由于装置中的电流特性的变化而导致发光亮度劣化的问题的层,并且它可以控制电荷流动特性。
除本文所公开的第二空穴传输层中包含式I与在发光层中式II,式III的特定组合之外,OLED器件中对于其他层材料并无特殊限制。可以使用现有的空穴注入材料、空穴输送材料、掺杂剂材料、空穴阻挡层材料、电子传输层材料和电子注入材料。
空穴注入层材料,有金属卟啉、低聚噻吩、芳基胺系衍生物、六腈六氮杂苯并菲系有机物、喹吖啶酮系有机物、苝系有机物、蒽醌及聚苯胺和聚噻吩系导电性高分子等,P掺杂的P掺杂剂可以通过下列化合物举例说明,但不仅限于此。
第一空穴传输材料,可以选自芳基胺系衍生物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等,具体的,第一空穴传输层材料选自如下化合物,但并非仅限于此。
本发明的第二空穴传输层为通式I所示化合物。
本发明的红光双主体材料为通式II,通式III所示化合物。
本发明掺杂剂材料选为红光掺杂材料,有芳香族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体的,本发明红光掺杂材料选自如下化合物,但并非仅限于此。
电子传输层(空穴阻挡层)的材料,噁唑,咪唑,噻唑,三嗪等衍生物,金属螯合物,喹啉衍生物,喔啉衍生物,二氮蒽衍生物,二氮菲衍生物,含硅的杂环化合物,全氟化的寡聚物等,具体的,电子传输层材料选自如下化合物,但并非仅限于此。
电子注入层的材料包括噁唑、噁二唑、***、咪唑、苝四羧酸、亚芴基甲烷、蒽酮以及它们的衍生物、镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡、镱等金属或它们的合金,金属配合物或含氮5元环衍生物等,但并不限于此。
以下结合具体实施例对本发明提供的一种有机电致发光组合物和有机电致发光器件进行具体说明。
一种红光有机电致发光器件的制备方法,包括以下步骤:
a、ITO阳极:将涂层厚度为150nm的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,然后转移至甩干机内进行甩干,最后用真空烘箱220℃烘烤2小时,烘烤结束后降温即可使用;以该基板为阳极,使用蒸镀机进行蒸镀器件工艺,在其上依次蒸镀其它功能层;
b、HIL(空穴注入层):以1Å/s的蒸镀速率,真空蒸镀空穴注入层材料HT1-12和P-9,其化学式如下所示;所述HT1-12和P-9的蒸镀速率比为97:3,厚度为10nm;
c、HTL(空穴传输层):以1.0Å/s的蒸镀速率,在空穴注入层上面真空蒸镀125nm的HT1-12作为空穴传输层;
d、第二空穴传输层:以1.0Å/s的蒸镀速率,在空穴传输层上面真空蒸镀90nm的本发明提供的式I所示的化合物作为第二空穴传输层;
e、EML(发光层):然后在上述第二空穴传输层上,以1Å/s的蒸镀速率,真空蒸镀总厚度为40nm的式II和式III所示的主体材料(Host)和掺杂材料(Dopant-R-1)作为发光层,其Host和Dopant的化学式如下所示,其中主体材料式II和式III蒸镀比例为4:6,而Host和Dopant-R-1的蒸镀速率比为97:3;
f、HBL(空穴阻挡层):以0.5Å/s的蒸镀速率,真空蒸镀厚度为5.0nm的空穴阻挡层HB;
g、ETL(电子传输层):以1Å/s的蒸镀速率,真空蒸镀厚度为30nm的ET-10和Liq作为电子传输层;其中ET-10和Liq的蒸镀速率比为1:1;
h、EIL(电子注入层):以0.5Å/s的蒸镀速率,蒸镀Yb膜层1.0nm,形成电子注入层;
i、阴极:以1Å/s的蒸镀速率比,蒸镀镁和银18nm,其蒸镀速率比为1:9,形成阴极;
j、光取出层:以1Å/s的蒸镀速率,在阴极上真空蒸镀厚度为70nm的CPL,作为光取出层;
k、将蒸镀完成的基板进行封装;首先采用涂胶设备将清洗后盖板用UV胶进行涂覆工艺,然后将涂覆完成的盖板移至压合工段,将蒸镀完成的基板置于盖板上端,最后将基板和盖板在贴合设备作用下进行贴合,同时完成对UV胶光照固化。
器件结构如下:
ITO/Ag/ITO/HT1-12:P-9(10nm)/HT1-12(125nm)/式I(90nm)/(式II+式III):Dopant-R-1 (40nm)/HB(5nm)/ET-10:Liq(30nm)/Yb(1nm)/Mg:Ag(18nm)/CPL(70nm)。
表1 各层所需材料
应用例1-9
按照上述有机电致发光器件的制备方法制备应用例1-9的有机电致发光器件,将表1中示出的化合物RH1-50,RH2-29作为主体材料,HT-4,HT-9,HT-11,HT-13,HT-22,HT-24,HT-25,HT-38,HT-52作为第二空穴传输层材料。
应用例10
按照上述有机电致发光器件的制备方法制备应用例10的有机电致发光器件,将表1中示出的化合物RH1-32,RH2-78作为主体材料,HT-13作为第二空穴传输层材料。
应用例11
按照上述有机电致发光器件的制备方法制备应用例11的有机电致发光器件,将表1中示出的化合物,RH1-57,RH2-5,作为主体材料,HT-13作为第二空穴传输层材料。
应用例12
按照上述有机电致发光器件的制备方法制备应用例12的有机电致发光器件,将表1中示出的化合物RH1-32,RH2-78作为主体材料,HT-24作为第二空穴传输层材料。
应用例13
按照上述有机电致发光器件的制备方法制备应用例13的有机电致发光器件,将表1中示出的化合物RH1-57,RH2-5作为主体材料,HT-24作为第二空穴传输层材料。
对比例1-3
按照上述有机电致发光器件的制备方法制备对比例1-3的有机电致发光器件,将表1中示出的化合物RH1-50,RH2-29作为主体材料,对比化合物1-对比化合物3作为第二空穴传输层材料。
对比例4
按照上述有机电致发光器件的制备方法制备对比例4的有机电致发光器件,将表1中示出的化合物RH1-32,RH2-78作为主体材料,对比化合物2作为第二空穴传输层材料。
对比例5
按照上述有机电致发光器件的制备方法制备对比例5的有机电致发光器件,将表1中示出的化合物RH1-57,RH2-5作为主体材料,对比化合物2作为第二空穴传输层材料。
在6000(nits)亮度下对上述器件应用例1-13以及器件对比例1-5得到的有机电致发光器件的驱动电压、启亮电压,测试结果请参阅表2和图1。
表2 测试结果(亮度值为6000 nits)
实施例 | 第二空穴传输层 | 主体1 | 主体2 | 启亮电压(V) | 驱动电压(V) |
应用例1 | HT-4 | RH1-50 | RH2-29 | 2.22 | 3.43 |
应用例2 | HT-9 | RH1-50 | RH2-29 | 2.21 | 3.43 |
应用例3 | HT-11 | RH1-50 | RH2-29 | 2.23 | 3.41 |
应用例4 | HT-13 | RH1-50 | RH2-29 | 2.26 | 3.45 |
应用例5 | HT-22 | RH1-50 | RH2-29 | 2.20 | 3.44 |
应用例6 | HT-24 | RH1-50 | RH2-29 | 2.24 | 3.46 |
应用例7 | HT-25 | RH1-50 | RH2-29 | 2.22 | 3.43 |
应用例8 | HT-38 | RH1-50 | RH2-29 | 2.23 | 3.44 |
应用例9 | HT-52 | RH1-50 | RH2-29 | 2.23 | 3.43 |
应用例10 | HT-13 | RH1-32 | RH2-78 | 2.24 | 3.45 |
应用例11 | HT-13 | RH1-57 | RH2-5 | 2.22 | 3.42 |
应用例12 | HT-24 | RH1-32 | RH2-78 | 2.24 | 3.43 |
应用例13 | HT-24 | RH1-57 | RH2-5 | 2.22 | 3.44 |
对比例1 | 对比化合物1 | RH1-50 | RH2-29 | 2.13 | 3.50 |
对比例2 | 对比化合物2 | RH1-50 | RH2-29 | 2.14 | 3.46 |
对比例3 | 对比化合物3 | RH1-50 | RH2-29 | 2.11 | 3.52 |
对比例4 | 对比化合物2 | RH1-32 | RH2-78 | 2.12 | 3.51 |
对比例5 | 对比化合物2 | RH1-57 | RH2-5 | 2.13 | 3.49 |
本发明中,将红光器件在6000 nits下的电压作为驱动电压。
由表2得到的启动电压与驱动电压显示,启亮电压提高在0.1-0.15V之间,在本领域已经是显著提高。本发明通过在空穴传输区域中包含本公开的式I所示的具有特定的芳基胺衍生物以及在发光层中包含本公开式II,式III所示的双主体红光材料特定组合制备成的有机电致发光器件,能够提高启亮电压并保持较低驱动电压。
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (9)
1.一种有机电致发光器件,包括第一电极、面向所述第一电极的第二电极、在所述第一电极与所述第二电极之间的发光层、以及在所述第一电极与所述发光层之间的空穴传输区域;其特征在于,所述空穴传输区域包括空穴注入层,第一空穴传输层,第二空穴传输层;
所述第二空穴传输层的结构通式如式I所示:
其中,
Ar’1,Ar’2各自独立地为取代或未取代的C6-C24芳基、取代或未取代的3元至24元杂芳基;
R’1-R’3各自独立地为氢、氘、取代或未取代的C1-C6烷基、取代或未取代的C6-C18芳基、取代或未取代的3元至18元杂芳基、取代或未取代的C3-C12环烷基、取代或未取代的C1-C6烷氧基;
R’4为氢,甲基,乙基,苯基或联苯基;
R’1-R’4与所在苯环以取代或形成稠合环的方式连接;
所述发光层包含P型主体材料和N型主体材料;
所述P型主体材料的结构通式如式II所示:
其中,
Y1,Y2选自如下组合:
Y1为N,Y2为O;
Y1为N,Y2为S;
Y1为O,Y2为N;
Y1为S,Y2为N;
L1为连接键、取代或未取代的C6-C18亚芳基、取代或未取代的3元至18元亚杂芳基;
Ar1-Ar3各自独立地为取代或未取代的C6-C24芳基、取代或未取代的3元至24元杂芳基;
Ar1-Ar3与所在苯环以取代或形成稠合环的方式连接;
所述N型主体材料的结构通式如式III所示:
其中,
X1选自O或S;
m,n,p中一个为1,其余为0;
Z1-Z3各自独立地为N或C,且至少一个为N;
Ar4-Ar5各自独立地为取代或未取代的C6-C24芳基、取代或未取代的3元至24元杂芳基;
L2为连接键、取代或未取代的C6-C18亚芳基、取代或未取代的3元至18元亚杂芳基。
8.一种有机电致发光装置,其特征在于,所述有机电致发光装置包含如权利要求1-7任一所述的有机电致发光器件,所述有机电致发光器件为顶部发光型、底部发光型或双向发光型。
9.一种光电设备,其特征在于,所述光电设备包含如权利要求1-7任一所述的有机电致发光器件,所述光电设备为有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
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