CN113582855B - 一种二胺类有机化合物及其有机发光器件 - Google Patents
一种二胺类有机化合物及其有机发光器件 Download PDFInfo
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- CN113582855B CN113582855B CN202110870457.8A CN202110870457A CN113582855B CN 113582855 B CN113582855 B CN 113582855B CN 202110870457 A CN202110870457 A CN 202110870457A CN 113582855 B CN113582855 B CN 113582855B
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- 239000012044 organic layer Substances 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 16
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000001975 deuterium Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 4
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- ZJFKMIYGRJGWIB-UHFFFAOYSA-N n-[3-methyl-4-[2-methyl-4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=CC=C1C(C(=C1)C)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ZJFKMIYGRJGWIB-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- CWIUXGVIFIAHGZ-UHFFFAOYSA-N n-[4-[4-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 CWIUXGVIFIAHGZ-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007738 vacuum evaporation 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
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 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
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
本发明提供一种二胺类有机化合物及其有机发光器件,涉及有机光电材料技术领域。该二胺类有机化合物,具有较高的玻璃化转化温度,有效地提高了有机发光器件的使用寿命。应用于有机发光器件中,提高空穴在器件中的传输效率,并将电子有效的阻挡在发光层内,实现了载流子的最大复合;同时降低空穴在注入过程中的能量壁垒,提高空穴的注入效率,从而提高有机发光器件的发光效率以及能够降低器件的驱动电压。并且,该二胺类有机化合物成膜性好,合成简单易操作,可广泛应用于面板显示、照明光源、有机太阳能电池、有机感光体或有机薄膜晶体管等领域。
Description
技术领域
本发明涉及有机光电材料技术领域,尤其涉及一种二胺类有机化合物及其有机发光器件。
背景技术
有机发光二极管(organic light emitting diode,OLED)因其重量轻、成本低、视角宽、响应速度快、主动发光和能实现全色显示等优点,备受科学界和产业界的重视。可以说,OLED具备了照明和信息显示器件制造所要求的几乎所有优异特征,被业界公认为是最理想和最具发展前景的下一代照明显示技术之一。由于OLED潜在的巨大应用价值,如何制备高效率的器件越来越吸引人们的广泛关注,同时,人们对OLED的性能要求也随之提高。
常见的有机发光器件是由阳极、阴极以及在阴极和阳极之间设置一层以上的有机层构成。当阴阳两极施加电压时,两电极产生电场,在电场的作用下,阴极侧的电子向发光层移动,阳极侧的空穴也向发光层移动,两者在发光层结合形成激子,激子处于激发态向外释放能量,从激发态释放能量变为基态释放能量的过程对外发光。因此,提高OLED器件中电子和空穴的再结合性是至关重要的。
为了提高有机发光器件的亮度、效率和寿命以及降低器件的驱动电压,通常在器件中使用多层结构。这些多层结构包括:空穴注入层、空穴传输层、电子阻挡层、发光层和电子传输层等等。这些有机层具有提高载流子(空穴和电子)在各层界面间的注入效率,平衡载流子在各层之间传输的能力,从而提高器件的亮度和效率。而空穴传输层的基本作用是提高空穴在器件中的传输效率,并将电子有效的阻挡在发光层内,实现载流子的最大复合;同时降低空穴在注入过程中的能量壁垒,提高空穴的注入效率,从而提高器件的效率和寿命。
由于器件在工作中要产生焦耳热,这些热量常常引起材料的再结晶。而结晶会破坏薄膜的均一性,同时破坏空穴传输层同阳极以及有机层之间良好的界面接触,导致器件的效率和寿命下降。并且空穴的迁移率过低,会使空穴和电子的注入不平衡,两者在发光层内不能有效的结合,导致有机发光器件发光效率降低。因此有机空穴传输材料的研究的重点在于提高材料的热稳定性以及空穴迁移率。如何设计新的性能更好的材料进行调节,以使所有器件能够达到降低电压、提高效率和寿命的效果,一直是本领域技术人员亟待解决的问题。
发明内容
本发明的目的在于,提供一种二胺类有机化合物及其有机发光器件,使用该二胺类有机化合物制备的有机发光器件具有良好的发光效率,较低的驱动电压以及良好的使用寿命;作为有机发光器件中的空穴传输层的主要构成成分,解决了上述问题,其分子结构通式如式Ⅰ所示:
其中,所述R0为氘原子、取代或未取代的C1~C10烷基、取代或未取代的C3~C12环烷基、取代或未取代的C6~C25的芳基中的一种;
m选自0至5的整数;
A相同或不同地为氢、取代或未取代的金刚烷基中的一种;
条件是:A或R0中至少有一个为取代或未取代的金刚烷基;
Ar1、Ar2独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的三亚苯基中的一种;
L1、L2、L3、L4独立地选自单键、取代或未取代的C6~C25亚芳基、取代或未取代的C2~C20亚杂芳基中的一种。
本发明还提供了一种有机发光器件,所述有机发光器件包括阴极、阳极和置于所述阴极和阳极之间及之外的一个或多个有机物层,所述置于阴极和阳极之间的有机物层包括空穴注入层、空穴传输层,电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层;所述置于阴极和阳极之外的有机物层包括覆盖层,本发明所述有机物层包括空穴传输层,空穴传输层中含有本发明所述的任一种二胺类有机化合物中的任意一种或至少两种的组合。
本发明的有益效果:
本发明提供一种二胺类有机化合物及其有机发光器件,本发明所述的二胺类有机化合物,双胺或桥连上至少一个为取代或未取代的金刚烷基,该二胺类有机化合物,提高了材料的玻璃化转化温度(Tg),以及蒸镀温度,控制材料的结晶性,有效地提高了有机发光器件的使用寿命。
本发明所述的二胺类有机化合物应用于有机发光器件中,提高空穴在器件中的传输效率,并将电子有效的阻挡在发光层内,实现载流子的最大复合;同时降低空穴在注入过程中的能量壁垒,提高空穴的注入效率,从而提高有机发光器件的发光效率以及能够降低器件的驱动电压。
本发明制备的有机发光器件大大改善了器件特性,有效地提高了有机发光器件的发光效率,降低了器件的驱动电压以及提高了器件的使用寿命,具有良好的应用效果和产业化前景。
具体实施方式
下面将结合本发明实施例的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明的保护范围。
在本说明书中,当取代基在芳香环上的位置不固定时,表示其可连接于所述芳香环的相应可选位点中的任一个,
例如,可表示/>以此类推。
本发明所述的烷基是指烷烃分子中少掉一个氢原子而成的烃基,其可以为直链烷基、支链烷基,优选具有1至15个碳原子,更优选1至12个碳原子,特别优选1至6个碳原子。所述直链烷基包括甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、十一烷基、十二烷基等,但不限于此;所述支链烷基包括异丙基、异丁基、仲丁基、叔丁基、正戊基的异构基团、正己基的异构基团、正庚基的异构基团、正辛基的异构基团、正壬基的异构基团、正癸基的异构基团等,但不限于此,但不限于此。上述烷基优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基。
本发明所述的环烷基是指环烷烃分子中少掉一个氢原子而成的烃基,优选具有3至15个碳原子,更优选3至12个碳原子,特别优选3至6个碳原子,实例可包括环丙基、环丁基、环戊基、环己基、金刚烷基、莰烷基、降冰片烷基等,但不限于此。上述烷基优选为环戊基、环己基、1-金刚烷基、2-金刚烷基、降冰片烷基。
本发明所述的芳基是指芳香族化合物分子的芳核碳上去掉一个氢原子后,剩下一价基团的总称,其可以为单环芳基、多环芳基或者稠环芳基,优选具有6至25个碳原子,更优选6至20个碳原子,特别优选6至14个碳原子。所述单环芳基是指分子中只有一个芳香环的芳基,例如,苯基等,但不限于此;所述多环芳基是指分子中含有两个或者两个以上独立芳香环的芳基,例如,联苯基、三联苯基等,但不限于此;所述稠环芳基是指分子中含有两个或者多个芳香环且彼此间通过共用两个相邻碳原子稠合而成的芳基,例如,萘基、蒽基、菲基、芘基、苝基、芴基、苯并芴基、三亚苯基、荧蒽基、螺二芴基等,但不限于此。上述芳基优选为苯基、联苯基、三联苯基、萘基(优选2-萘基)、蒽基(优选2-蒽基)、菲基、芘基、苝基、芴基、苯并芴基、三亚苯基、螺二芴基。
本发明所述的杂芳基是指芳基中的一个或多个芳核碳原子被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫、氮或者磷原子,优选具有1至25个碳原子,更优选2至20个碳原子,特别优选3至12个碳原子,所述杂芳基的连接位点可以位于成环碳原子上,也可以位于成环氮原子上,所述杂芳基可以为单环杂芳基、多环杂芳基或者稠环杂芳基。所述单环杂芳基包括吡啶基、嘧啶基、三嗪基、呋喃基、噻吩基、吡咯基、咪唑基等,但不限于此;所述多环杂芳基包括联吡啶基、联嘧啶基、苯基吡啶基等,但不限于此;所述稠环杂芳基包括喹啉基、异喹啉基、吲哚基、苯并噻吩基、苯并呋喃基、苯并噁唑基、苯并咪唑基、苯并噻唑基、二苯并呋喃基、苯并二苯并呋喃基、二苯并噻吩基、苯并二苯并噻吩基、咔唑基、苯并咔唑基、吖啶基、9,10-二氢吖啶基、吩噁嗪基、吩噻嗪基、吩噁噻基等,但不限于此。上述杂芳基优选为吡啶基、嘧啶基、噻吩基、呋喃基、苯并噻吩基、苯并呋喃基、苯并噁唑基、苯并咪唑基、苯并噻唑基、二苯并呋喃基、二苯并噻吩基、苯并二苯并噻吩基、苯并二苯并呋喃基、咔唑基、吖啶基、吩噁嗪基、吩噻嗪基、吩噁噻基。
本发明所述的亚芳基是指芳香族化合物分子的芳核碳上去掉两个氢原子后,剩下二价基团的总称,其可以为单环亚芳基、多环亚芳基或者稠环亚芳基,优选具有6至25个碳原子,更优选6至20个碳原子,特别优选6至14个碳原子。所述单环亚芳基包括亚苯基等,但不限于此;所述多环亚芳基包括亚联苯基、亚三联苯基等,但不限于此;所述稠环亚芳基包括亚萘基、亚蒽基、亚菲基、亚芴基、亚芘基、亚三亚苯基、亚荧蒽基、亚苯基芴基等,但不限于此。上述亚芳基优选为亚苯基、亚联苯基、亚三联苯基、亚萘基、亚芴基、亚苯基芴基。
本发明所述的亚杂芳基是指亚芳基中的一个或多个芳核碳被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫、氮或者磷原子。优选具有1至25个碳原子,更优选2至20个碳原子,特别优选3至12个碳原子,所述亚杂芳基的连接位点可以位于成环碳原子上,也可以位于成环氮原子上,所述亚杂芳基可以为单环亚杂芳基、多环亚杂芳基或者稠环亚杂芳基。所述单环亚杂芳基包括亚吡啶基、亚嘧啶基、亚三嗪基、亚呋喃基、亚噻吩基等,但不限于此;所述多环亚杂芳基包括亚联吡啶基、亚联嘧啶基、亚苯基吡啶基等,但不限于此;所述稠环亚杂芳基包括亚喹啉基、亚异喹啉基、亚吲哚基、亚苯并噻吩基、亚苯并呋喃基、亚苯并噁唑基、亚苯并咪唑基、亚苯并噻唑基、亚二苯并呋喃基、亚苯并二苯并呋喃基、亚二苯并噻吩基、亚苯并二苯并噻吩基、亚咔唑基、亚苯并咔唑基、亚吖啶基、亚9,10-二氢吖啶基、亚吩噁嗪基、亚吩噻嗪基、亚吩噁噻基等,但不限于此。上述杂芳基优选为亚吡啶基、亚嘧啶基、亚噻吩基、亚呋喃基、亚苯并噻吩基、亚苯并呋喃基、亚苯并噁唑基、亚苯并咪唑基、亚苯并噻唑基、亚二苯并呋喃基、亚二苯并噻吩基、亚苯并二苯并噻吩基、亚苯并二苯并呋喃基、亚咔唑基、亚吖啶基、亚吩噁嗪基、亚吩噻嗪基、亚吩噁噻基。
本发明所述的甲硅烷基是指甲硅烷化合物分子中少掉一个氢原子后,剩下一价基团的总称,可以包括烷基甲硅烷基或芳基甲硅烷基。所述甲硅烷基包括三甲基甲硅烷基,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。上述甲硅烷基优选为三甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基。
本发明所述“取代的…”诸如取代的烷基、取代的环烷基、取代的芳基、取代的杂芳基、取代的亚芳基、取代的亚杂芳基是指被独立地选自氘基、卤素、氰基、取代或未取代的C1~C15烷基、取代或未取代的C3~C15环烷基、取代或未取代的C6~C25芳基、取代或未取代的C2~C20杂芳基、取代或未取代的胺基等但不限于此的基团单取代或多取代,优选被选自氘基、氟、氯、溴、碘、氰基、甲基、乙基、异丙基、叔丁基、苯基、联苯基、三联苯基、萘基、蒽基、菲基、苯并菲基、三亚苯基、苝基、芘基、苯甲基、芴基、9,9-二甲基芴基、9,9-二苯基芴基、二苯胺基、二甲胺基、咔唑基、9-苯基咔唑基、吖啶基、呋喃基、噻吩基、苯并呋喃基、苯并噻吩基、苯并噁唑基、苯并咪唑基、苯并噻唑基、二苯并呋喃基、二苯并噻吩基、吩噻嗪基、吩噁嗪基、吲哚基的基团单取代或多取代。
本发明所述的“选自0~M的整数”是指所述值选自0~M的整数中的任意一个,包括0,1,2…M-2,M-1,M。例如,“m选自0至5的整数”是指m选自0,1,2,3,4,5;“p选自0至5的整数”是指p选自0,1,2,3,4,5;“q选自0至5的整数”是指a选自0,1,2,3,4,5;以此类推。
本发明提供了一种二胺类有机化合物,其分子结构通式如式Ⅰ所示:
其中,所述R0为氘原子、取代或未取代的C1~C10烷基、取代或未取代的C3~C12环烷基、取代或未取代的C6~C25的芳基中的一种;
m选自0至5的整数;
A相同或不同地为氢、取代或未取代的金刚烷基中的一种;
条件是:A或R0中至少有一个为取代或未取代的金刚烷基;
Ar1、Ar2独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的三亚苯基中的一种;
L1、L2、L3、L4独立地选自单键、取代或未取代的C6~C25亚芳基、取代或未取代的C2~C20亚杂芳基中的一种。
优选的,所述R0为氢原子、氘原子、金刚烷基、甲基、乙基、异丙基、叔丁基、环戊基、环己基、莰烷基、降冰片烷基、苯基、甲苯基、萘基中的一种。
优选的,所述式Ⅰ选自如下式Ⅰ-1至式Ⅰ-6中的一种:
其中,p选自1至5的整数;q选自1至5的整数。
优选的,所述取代或未取代的金刚烷基选自如下式Ⅱ基团:
R为氢、氘原子、卤素原子、氰基、取代的或未取代的甲硅烷基、取代或未取代的C1~C10的烷基、取代或未取代的C3~C12的环烷基、取代或未取代的C6~C25的芳基、取代或未取代的C2~C20杂芳基;
n选自0至15的整数。
优选的,所述式Ⅱ基团选自如下式Ⅱ-1或式Ⅱ-2所示基团:
其中,R为氢、氘原子、甲基、乙基、异丙基、叔丁基、环己基、苯基、甲苯基、联苯基、萘基中的一种;n选自0至6的整数。
优选的,所述式Ⅱ基团选自如下式II-1或式II-21所示基团:
优选的,所述Ar1、Ar2独立地选自如下基团中的一种:
优选的,所述Ar1、Ar2独立地选自如下基团中的一种:
优选的,所述L1、L2、L3、L4独立地选自单键或如下所示基团中的任意一种:
优选的,所述L1、L2、L3、L4独立地选自单键或如下所示基团中的任意一种:
优选的,本发明的二胺类有机化合物选自如下所示化学结构中的任意一种:
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本发明式I所述的二胺类有机化合物的制备方法,可通过本领域常规的偶联反应即可制备得到,例如可通过如下合成路线制备得到,但本发明不限于此:
本发明化合物可先通过铃木反应得到中间体C,再与胺化合物发生布赫瓦尔德反应得到化学式Ⅰ所示目标化合物,即在氮气气氛下,加入原料、催化剂、碱、配体及溶液,并在相应温度下反应获得,其中X0代表卤素如Cl、Br、I。
本发明对上述各类反应中所采用的原料的来源没有特别的限制,可以使用市售产品原料或采用本领域技术人员所熟知的制备方法得到。本发明对上述反应没有特殊的限制,采用本领域技术人员所熟知的常规反应即可。本发明所述化合物合成步骤少、方法简单,有利于工业化生产。
本发明还提供了一种有机发光器件,所述有机发光器件包括阴极、阳极、置于所述阴极和阳极之间的一个或多个有机物层及置于所述阴极和阳极之外的一个或多个有机物层,所述置于阴极和阳极之间的有机物层包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、中的至少一层;所述置于阴极和阳极之外的有机物层包括空穴传输层,所述空穴传输层中含有本发明所述的任一种二胺类有机化合物的任意一种或至少两种的组合。
本发明的发光器件通常在基板上形成。上述基板只要在形成电极、形成有机物层时不发生变化即可,例如,玻璃、塑料、高分子薄膜、硅等的基板。当基板不透明时,与其相对的电极优选为透明或者半透明的。
本发明的发光器件所具有的阳极和阴极中的至少一方为透明或者半透明的,优选的,本发明所述在阳极侧为透明或者半透明的。
阳极材料,通常优选具有大功函数的材料,使得空穴顺利地注入有机材料层,常使用导电性的金属氧化物膜、半透明的金属薄膜等。例如,使用含有氧化铟、氧化锌、氧化锡、以及作为它们的复合体的氧化铟锡(简称:ITO)、氧化铟锌(简称:IZO)等导电性无机化合物制成的膜(NESA等)或使用金、铂、银、铜等,作为其制作方法,可举出真空蒸镀法、溅射法、离子镀法、镀敷法等。另外,作为该阳极,可以使用聚苯胺或其衍生物、聚噻吩或其衍生物等有机的透明导电膜。予以说明,可以将阳极形成2层以上的积层结构,优选的,本发明所述阳极采用透明的ITO基板。
空穴注入层是提高空穴从阳极注入空穴传输层和发光层的效率。本发明的空穴注入材料可以采用钼氧化物、银氧化物、钒氧化物、钨氧化物、钌氧化物、镍氧化物、铜氧化物、钛氧化物等金属氧化物,酞菁类化合物、含有多氰基的共轭有机材料等低分子有机化合物,但不限于此。其可以是单一物质构成的单一结构,也可是不同物质形成的单层或多层结构。
空穴传输层为具有传输空穴的功能的层。本发明的空穴传输材料优选具有较好的空穴传输性能的材料,可以选择芳香族胺类衍生物、咔唑衍生物、芪衍生物、三苯基二胺衍生物、苯乙烯类化合物、丁二烯类化合物等小分子材料以及聚对苯撑衍生物、聚苯胺及其衍生物、聚噻吩及其衍生物、聚乙烯基咔唑及其衍生物、聚硅烷及其衍生物等聚合物材料及本发明提供的一种二胺类有机化合物,但不限于此。优选的,空穴传输层选自本发明所述的二胺类有机化合物,其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。
电子阻挡层是将输送空穴、且封闭电子的层,优选的,本发明所述电子阻挡层可选自N,N'-二(萘-1-基)-N,N'-二(苯基)-2,2'-二甲基联苯胺(简称:α-NPD)、4,4',4”-三(N,N-二苯基氨基)三苯胺(简称:TDATA)、N,N'-二苯基-N,N'-二(3-甲基苯基)-1,1'-联苯-4,4'-二胺(简称:TPD)、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](简称:TAPC)、2,2,7,7-四(二苯基氨基)-9,9-螺二芴(简称:Spiro-TAD)等,其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。除了以上材料及其组合之外,电子阻挡层材料还可包括其他已知的适合做电子阻挡层的材料。
发光层为具有发光功能的层。关于本发明有机发光器件的发光层,发光材料可使用红色发光材料、绿色发光材料、或蓝色发光材料,如果需要,也可将两种或更多种发光材料进行混合使用。此外,作为发光材料,可以仅为主体材料,也可以是主体材料和掺杂材料的混合物,优选发光层由主体材料和掺杂材料混合使用。
优选的,本发明所述主体材料选自4,4'-二(9-咔唑)联苯(简称:CBP)、9,10-二(2-萘基)蒽(简称:ADN)、4,4-二(9-咔唑基)联苯(简称:CPB)、9,9'-(1,3-苯基)二-9H-咔唑(简称:mCP)、4,4',4”-三(咔唑-9-基)三苯胺(简称:TCTA)、9,10-二(1-萘基)蒽(简称:α-AND)、N,N'-二-(1-萘基)-N,N'-二苯基-[1,1':4',1”:4”,1”'-四联苯]-4,4”'-二胺基(简称:4P-NPB)、1,3,5-三(9-咔唑基)苯(简称:TCP)等,其可以是单一物质构成的单层结构,也可是不同物质形成的单层结构或多层结构,除了以上材料及其组合之外,发光层主体材料还可包括其他已知的适合做发光层的材料,例如如下GH-1至GH-12表示的绿色发光层主体材料:
本发明的发光层客体材料可以包含一种材料或两种以上的混合材料,发光材料分为蓝色发光材料、绿色发光材料以及红色发光材料。优选的,本发明发光材料选用绿色发光材料,所述绿色发光层客体选自三(2-苯基吡啶)合铱(Ir(ppy)3)、乙酰丙酮酸二(2-苯基吡啶)铱(Ir(ppy)2(acac))等。除了以上材料之外,发光层客体材料还可包括其他已知的适合做发光层的材料。
作为发光层主体材料和发光层客体材料的掺杂比例,其最佳可根据所用的材料而不同,通常发光层客体材料质量百分比例为0.01%~20%,优选为0.1%~15%,更优选为1%~10%。
空穴阻挡层是输送电子、且封闭空穴的层,优选的,本发明所述的空穴阻挡层选自2,9-二甲基-4,7-二苯基-1,10-菲啰啉(简称:BCP)、1,3,5-三(N-苯基-2-苯并咪唑)苯(简称:TPBi)、三(8-羟基喹啉)合铝(III)(简称:Alq3)、8-羟基喹啉-锂(简称:Liq)、二(2-甲基-8-羟基喹啉)(4-苯基苯酚)合铝(III)(简称:BAlq)及3-(联苯-4-基)-5-(4-叔丁基苯基)-4-苯基-4H-1,2,4-三唑(简称:TAZ)等,其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。
电子传输层为具有传输电子的功能的层,起到注入电子和平衡载流子的作用。本发明所述的电子传输材料,可选自公知的噁二唑衍生物、蒽醌二甲烷及其衍生物、苯醌及其衍生物、萘醌及其衍生物、蒽醌及其衍生物、四氰基蒽醌二甲烷及其衍生物、芴酮衍生物、联对苯醌衍生物、8-羟基喹啉及其衍生物的金属络合物。本发明的电子传输层可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。除了以上材料之外,电子传输层材料还可包括其他已知的适合做电子传输层的材料。优选的,本发明所述电子传输层选自如下化合物的一种或多种的混合。
电子注入层材料是辅助电子从阴极注入到有机层的材料。该材料的最佳选择通常为抗腐蚀性的高功函数的金属为阴极,常用的材料为Al和Ag。电子注入材料发展到目前,包括两类;一类是碱金属化合物,如氧化锂(Li2O)、氧化锂硼(LiBO2)、碳酸铯(Cs2CO3)、硅酸钾(K2SiO3)等,最佳厚度一般为0.3~1.0nm,此类化合物组成的器件能够降低驱动电压并提高器件效率。此外,碱金属的醋酸盐类化合物(CH3COOM,其中M为Li、Na、K、Rb、Cs)也具有相似的效果。另一类是碱金属氟化物(MF,其中M为Li、Na、K、Rb、Cs),如果用Al做阴极材料,这些材料的最佳厚度通常小于1.0nm。优选的,本发明所述的电子注入层可以选自LiF。
阴极材料,为了将电子注入到电子注入/输送层或者发光层,通常优选功函数小的金属材料。可以使用例如,锂、钠、钾、铷、铯、铍、镁、钙、锶、钡、铝、钪、钒、锌、钇、铟、铈、钐、铕、铽、镱等金属以及它们中的2种以上形成的合金、或者它们中的1种以上与金、银、铂、铜、锰、钛、钴、镍、钨、锡中的1种以上形成的合金、石墨或者石墨层间化合物等。作为合金,可举出镁-银合金、镁-铟合金、镁-铝合金、铟-银合金、锂-铝合金、锂-镁合金、锂-铟合金、钙-铝合金等。予以说明,可以将阴极形成2层以上的积层结构。该阴极可以通过将这些电极物质用蒸镀法或溅射法等方法形成薄膜来制备。其中,当从阴极取出发光层的发光时,优选阴极的光透过率大于10%。还优选阴极的片材电阻率为数百Ω/□以下,膜厚通常为10nm~1μm,优选50~200nm。
优选的,本发明所述阴极采用Ag或Al。
作为空穴传输层和电子传输层的膜厚,其最佳可根据所用的材料而不同,只要按照能使驱动电压和发光效率达到适度的值的条件来选择即可,但是必须至少不会导致发生针孔的厚度,如果过厚,则器件的驱动电压提高,是不理想的。因此该空穴传输层和电子传输层的膜厚例如为1nm~1um,优选为2nm~500nm,更优选为5nm~200nm。
关于积层的层的顺序和层数及各层的厚度,可以考虑发光效率和器件的寿命来适宜选择。
本发明所述的有机发光器件其结构优选为:
基板/阳极/空穴传输层/发光层/阴极;
基板/阳极/空穴传输层/发光层/电子传输层/阴极;
基板/阳极/空穴传输层/发光层/电子传输层/阴极/覆盖层;
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/阴极;
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/阴极/覆盖层;
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/阴极;
基板/阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极;
基板/阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极/覆盖层;
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/阴极;
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/阴极/覆盖层;
然而,有机发光器件的结构不限于此。本发明所述的有机发光器件可根据器件参数要求及材料的特性进行选择及组合,也可增加或省略部分有机层。例如,在所述电子传输层与所述发光层之间还可以具有空穴阻挡层,还可以将具有相同功能的有机层制成两层以上的层叠结构。
有机发光器件中各层的制备形成方法,没有特别限制,可以采用真空蒸镀法、旋涂法、气相沉积法、刮涂法、激光热转印法、电喷涂布法、狭缝式涂布法、浸沾式涂布法中的任意一种,在本发明中优选采用真空蒸镀的方法。
本发明所述有机发光器件可广泛应用于面板显示、照明光源、柔性OLED、电子纸、有机太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。
通过以下实施例,更详尽地解释本发明,但不希望因此限制本发明。在该描述的基础上,本领域普通技术人员将能够在不付出创造性劳动的情况下,在所公开的整个范围内实施本发明和制备根据本发明的其他化合物和器件。
化合物的制备及表征
原料、试剂以及表征设备的说明:
本发明对以下实施例中所采用的原料来源没有特别的限制,可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
质谱使用英国沃特斯G2-Si四极杆串联飞行时间高分辨质谱仪,氯仿为溶剂;
元素分析使用德国Elementar公司的Vario EL cube型有机元素分析仪,样品质量为5~10mg;
中间体的制备
1:合成中间体A-2
氩气氛下,化合物1-1(21.51g,100mmol)、1-2(17.27g,110mmol),溶于1000ml醋酸中,升温至80~90℃,滴加浓硫酸(2mmol),此体系温度下,恒温反应5h,加入1200ml水,降至室温以下搅拌析出大量固体,过滤,乙醇淋洗,可得到20.96g中间体A-2,产率为72%。质谱m/z:290.0686(理论值:290.0670)。
2:合成中间体A-3
在氩气氛下,将化合物2-2(15.22g,100mmol)和1-4(21.12g,102mmol)加入150ml二氯甲烷溶剂中,室温搅拌溶解,降温至10-15℃,且在保护下滴加浓硫酸(19.61g,200mmol),保温反应5h。向反应液中加入500ml去离子水水洗至pH=7,加入100ml二氯甲烷进行萃取,合并有机相,使用无水硫酸钠进行干燥,过滤,减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,得到中间体A-3(29.69g),产率87%。质谱m/z:340.0820(理论值:340.0827)。
3:合成中间体C-2
氩气氛下,a-2(14.56g,50mmol)、b-1(7.16g,50mmol)、叔丁醇钠(9.61g,100mmol)溶于250ml脱水甲苯,搅拌下加入醋酸钯(0.56g,2.5mmol)、三苯基膦(5.01g,2.5mmol),在100℃下反应8h。反应结束后,将混合物冷却至室温,用硅藻土过滤,浓缩滤液,用甲苯重结晶,抽滤并用甲苯淋洗得重结晶固体,得到中间体C-1(14.84g),产率为84%。质谱m/z:353.2154(理论值:353.2143)。
本发明中,中间体C-1,C-3~C-8均可以用以上制备方法制得,如下表所示:
合成实施例1:化合物2的制备
氩气氛下,D-1(7.8g,25mmol)、C-2(17.67g,50mmol)、叔丁醇钠(4.81g,50mmol)溶于150ml脱水甲苯,搅拌下加入醋酸钯(0.28g,1.25mmol)、三苯基膦(2.50g,1.25mmol),在100℃下反应8h。反应结束后,将混合物冷却至室温,用硅藻土过滤,浓缩滤液,用甲苯重结晶,抽滤并用甲苯淋洗得重结晶固体,得到化合物2(18.85g),产率为88%,HPLC检测固体纯度≧99.5%。质谱m/z:856.4799(理论值:856.4756)。理论元素含量(%)C64H60N2:C,89.68;H,7.06;N,3.27。实测元素含量(%):C,89.62;H,7.09;N,3.28。
合成实施例2:化合物3的制备
将合成实施例1中的C-2换成等摩尔的C-1,其他步骤相同,得到化合物3(18.64g),产率为87%,HPLC检测固体纯度≧99.4%。质谱m/z:856.4722(理论值:856.4756)。理论元素含量(%)C64H60N2:C,89.68;H,7.06;N,3.27。实测元素含量(%):C,89.72;H,7.07;N,3.22。
合成实施例3:化合物4的制备
将合成实施例1中的C-2换成等摩尔的C-3,其他步骤相同,得到化合物4(20.23g),产率为89%,HPLC检测固体纯度≧99.6%。质谱m/z:908.5102(理论值:908.5070)。理论元素含量(%)C68H64N2:C,89.82;H,7.09;N,3.08。实测元素含量(%):C,89.83;H,7.08;N,3.08。
合成实施例4:化合物5的制备
将合成实施例1中的C-2换成等摩尔的C-4,其他步骤相同,得到化合物5(18.42g),产率为86%,HPLC检测固体纯度≧99.8%。质谱m/z:856.4725(理论值:856.4756)。理论元素含量(%)C64H60N2:C,89.68;H,7.06;N,3.27。实测元素含量(%):C,89.65;H,7.05;N,3.33。
合成实施例5:化合物7的制备
将合成实施例1中的C-2换成等摩尔的C-6,其他步骤相同,得到化合物7(21.44g),产率为85%,HPLC检测固体纯度≧99.5%。质谱m/z:1008.5344(理论值:1008.5383)。理论元素含量(%)C76H68N2:C,90.43;H,6.79;N,2.78。实测元素含量(%):C,90.46;H,6.77;N,2.74。
合成实施例6:化合物8的制备
将合成实施例1中的C-2换成等摩尔的C-5,其他步骤相同,得到化合物8(17.64g),产率为81%,HPLC检测固体纯度≧99.6%。质谱m/z:870.5661(理论值:870.5635)。理论元素含量(%)C64H46D14N2:C,88.23;H,8.56;N,3.22。实测元素含量(%):C,88.24;H,8.56;N,3.25。
合成实施例7:化合物21的制备
将合成实施例1中的C-2换成等摩尔的C-5,其他步骤相同,得到化合物21(17.99g),产率为83%,HPLC检测固体纯度≧99.8%。质谱m/z:866.5398(理论值:866.5384)。理论元素含量(%)C64H50D10N2:C,88.64;H,8.13;N,3.23。实测元素含量(%):C,88.65;H,8.17;N,3.21。
合成实施例8:化合物23的制备
将合成实施例1中的C-2换成等摩尔的C-8,其他步骤相同,得到化合物23(19.62g),产率为82%,HPLC检测固体纯度≧99.6%。质谱m/z:956.5039(理论值:956.5070)。理论元素含量(%)C72H64N2:C,90.33;H,6.74;N,2.93。实测元素含量(%):C,90.32;H,6.77;N,2.94。
合成实施例9:化合物49的制备
Step1:合成中间体D-2
氮气氛围下,将化合物1-3(8.1g,50mmol)和2-1(18.82g,52mmol)溶解于150ml四氢呋喃(THF)中,再加入1.097g(1.5mmol)(1,1'-双(二苯基膦)二茂铁)二氯钯(II)以及CH3COOK(9.81g,100mmol)加入,搅拌混合物,将上述反应物的混合溶液于反应温度80℃下加热回流8h,反应结束后,冷却至室温,用去离子水和甲苯萃取,得到有机层,用400mL去离子水洗涤有机层3次,无水硫酸镁干燥后,减压浓缩,甲苯重结晶,得到中间体D-2(13.47g),产率为85%。质谱m/z:159.4726(理论值:159.4719)。
Step2:合成化合物49
将合成实施例1中的D-1换成等摩尔的D-2,C-2换成等摩尔的C-1,其他步骤相同,得到化合物49(17.89g),产率为83%,HPLC检测固体纯度≧99.4%。质谱m/z:861.5035(理论值:861.5070)。理论元素含量(%)C64H55D5N2:C,89.15;H,7.60;N,3.25。实测元素含量(%):C,89.19;H,7.58;N,3.27。
合成实施例10:化合物69的制备
Step1:合成中间体D-3
将合成实施例9中的化合物1-3换成等摩尔的A-1,其他步骤相同,得到19.48g中间体D-3,产率为87%。质谱m/z:149.3422(理论值:149.3408)
Step2:合成化合物69
将合成实施例1中的D-1换成等摩尔的D-3,C-2换成等摩尔的C-4,其他步骤相同,得到化合物69(20.82g),产率为84%,HPLC检测固体纯度≧99.4%。质谱m/z:990.5899(理论值:990.5852)。理论元素含量(%)C74H74N2:C,89.65;H,7.52;N,2.83。实测元素含量(%):C,89.69;H,7.50;N,2.81。
合成实施例11:化合物87的制备
用合成实施例9中,合成中间体D-2的方法合成中间体D-6,将合成实施例1中的D-1换成等摩尔的D-6,其他步骤相同,得到化合物87(18.83g),产率为83%,HPLC检测固体纯度≧99.2%。质谱m/z:906.4954(理论值:906.4913)。理论元素含量(%)C68H62N2:C,90.02;H,6.89;N,3.09。实测元素含量(%):C,90.09;H,6.93;N,3.01。
合成实施例12:化合物125的制备
将合成实施例1中的D-1换成等摩尔的D-5,其他步骤相同,得到化合物125(19.13g),产率为82%,HPLC检测固体纯度≧99.5%。质谱m/z:932.5089(理论值:932.5070)。理论元素含量(%)C70H64N2:C,90.09;H,6.91;N,3.00。实测元素含量(%):C,90.13;H,6.88;N,3.04。
合成实施例13:化合物208的制备
Step1:合成中间体D-5
氩气氛下,D-4(13.37g,50mmol)、C-3(18.97g,50mmol)、叔丁醇钠(8.65g,100mmol)溶于150ml脱水甲苯,搅拌下加入醋酸钯(0.56g,2.5mmol)、三苯基膦(0.65g,2.5mmol),在100℃下反应8h。反应结束后,将混合物冷却至室温,用硅藻土过滤,浓缩滤液,用甲苯重结晶,抽滤并用甲苯淋洗得重结晶固体,得到中间体D-5(24.62g),产率为87%。
Step2:合成化合物208
氩气氛下,D-5(14.15g,25mmol)、C-4(8.83g,25mmol)、叔丁醇钠(4.80g,50mmol)溶于150ml脱水甲苯,搅拌下加入醋酸钯(0.28g,1.25mmol)、三苯基膦(0.25g,1.25mmol),在110℃下反应8h。反应结束后,将混合物冷却至室温,用硅藻土过滤,浓缩滤液,用甲苯重结晶,抽滤并用甲苯淋洗得重结晶固体,得到化合物208(18.54g),产率为84%,HPLC检测固体纯度≧99.7%。质谱m/z:882.4959(理论值:882.4913)。理论元素含量(%)C66H62N2:C,89.75;H,7.08;N,3.17。实测元素含量(%):C,89.69;H,7.06;N,3.19。
合成实施例14:化合物209的制备
将合成实施例1中的C-2换成等摩尔的C-209,其他步骤相同,得到化合物209(15.54g),产率为86%,HPLC检测固体纯度≧99.4%。质谱m/z:722.3698(理论值:722.3661)。理论元素含量(%)C54H46N2:C,89.71;H,6.41;N,3.87。实测元素含量(%):C,89.72;H,6.38;N,3.86。
[对比实施例1]器件制备实施例:
对比实施例1:利用真空热蒸镀的方法制备有机发光器件。实验步骤为:将ITO透明基板放在蒸馏水中清洗3次,超声波洗涤15分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后,120℃烘干干燥,送到蒸镀机里。
在已经准备好的ITO透明基板电极上以逐层真空蒸镀的方式蒸镀空穴注入层2T-NATA/50nm、蒸镀空穴传输层HT-1/30nm、蒸镀发光层(主体GH-1:GH-2:Ir(ppy)3(45%:45%:10%混合))/30nm、然后蒸镀电子传输层ET-12/30nm、电子注入层LiF/0.5nm、阴极Al/120nm。并将该器件密封于手套箱中,从而制备了有机发光器件。按照上述步骤完成有机发光器件的制作后,测量器件的光电性能,相关材料的分子结构式如下所示:
[器件实施例1-14]
器件实施例1-14:将有机发光器件的空穴传输层材料依次换成本发明的化合物2、3、4、5、7、8、21、23、49、69、87、125、208、209,其他步骤均与对比实施例1相同。
将测试软件、计算机、美国Keithley公司生产的K2400数字源表和美国PhotoResearch公司的PR788光谱扫描亮度计组成一个联合IVL测试系统来测试有机发光器件的驱动电压、发光效率。寿命的测试采用McScience公司的M6000OLED寿命测试系统。测试的环境为大气环境,温度为室温。所得有机发光器件的发光特性测试结果见表1所示。表1为本发明实施例制备的化合物以及比较物质制备的发光器件的发光特性测试结果。
[表1]发光器件的发光特性测试
注:T97指的是在电流密度为10mA/cm2情况下,器件亮度衰减到97%所用的时间;
由表1的结果可以看出,本发明的二胺类有机化合物应用于有机发光器件中,尤其是作为空穴传输层材料,与对比实施例1-对比实施例2相比,表现出发光效率高,驱动电压低,使用寿命长的优点,是性能良好的有机发光材料。
应当指出,本发明用个别实施方案进行了特别描述,但在不脱离本发明原理的前提下,本领域普通技术人可对本发明进行各种形式或细节上的改进,这些改进也落入本发明的保护范围内。
Claims (8)
1.一种二胺类有机化合物,其特征在于,分子结构如式Ⅰ所示:
其中,所述R0为氘原子、取代或未取代的金刚烷基、甲基、乙基、异丙基、叔丁基、苯基、甲苯基、萘基中的一种;
m选自0至5的整数;当R0选自金刚烷基、苯基、甲苯基、萘基时,m选自1;
A相同地为氢、取代或未取代的金刚烷基中的一种;
条件是:A或R0中至少有一个为取代或未取代的金刚烷基;
所述Ar1、Ar2独立地选自如下基团中的一种:
L1、L2独立地选自如下所示基团中的任意一种:
L3、L4独立地选自单键或如下所示基团中的任意一种:
所述取代或未取代的金刚烷基选自如下式Ⅱ基团:
R为氢、氘原子、甲基;
n选自0至15的整数。
2.根据权利要求1所述的一种二胺类有机化合物,其特征在于,所述R0为氘原子、金刚烷基、苯基中的一种。
3.根据权利要求1所述的一种二胺类有机化合物,其特征在于,所述式Ⅰ选自如下式Ⅰ-1至式Ⅰ-6中的一种:
其中,p选自1至5的整数;
q选自1至5的整数。
4.根据权利要求1所述的一种二胺类有机化合物,其特征在于,所述式Ⅱ基团选自如下式Ⅱ-1或式Ⅱ-2所示基团:
其中,R为氢、氘原子、甲基中的一种;
n选自0至6的整数。
5.根据权利要求1所述的一种二胺类有机化合物,其特征在于,所述Ar1、Ar2独立地选自如下基团中的一种:
6.根据权利要求1所述的一种二胺类有机化合物,其特征在于,
L1、L2独立地选自如下所示基团中的任意一种:
L3、L4独立地选自单键或如下所示基团中的任意一种:
7.一种二胺类有机化合物,其特征在于,所述二胺类有机化合物选自如下所示化学结构中的任意一种:
8.一种有机发光器件,其特征在于,所述有机发光器件包括阴极、阳极、置于所述阴极和阳极之间的一个或多个有机物层及置于所述阴极和阳极之外的一个或多个有机物层,所述置于阴极和阳极之间的有机物层包括空穴传输层;所述置于阴极和阳极之外的有机物层包括覆盖层,所述空穴传输层中含有权利要求1~7任一项所述的二胺类有机化合物中的任意一种或至少两种的组合。
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