CN113061150B - 含磷有机化合物及其应用 - Google Patents
含磷有机化合物及其应用 Download PDFInfo
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- CN113061150B CN113061150B CN202110368208.9A CN202110368208A CN113061150B CN 113061150 B CN113061150 B CN 113061150B CN 202110368208 A CN202110368208 A CN 202110368208A CN 113061150 B CN113061150 B CN 113061150B
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- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 24
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 23
- 239000011574 phosphorus Substances 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 47
- 239000010410 layer Substances 0.000 claims description 59
- 230000000903 blocking effect Effects 0.000 claims description 8
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- 230000005669 field effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 80
- 238000002360 preparation method Methods 0.000 description 47
- 239000000543 intermediate Substances 0.000 description 32
- 125000003118 aryl group Chemical group 0.000 description 28
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- -1 aliphatic hydrocarbon radicals Chemical class 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 238000001308 synthesis method Methods 0.000 description 19
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- 150000003254 radicals Chemical group 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
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- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 4
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- ALTSSZFRWDVXPB-UHFFFAOYSA-N [9-(3-phenylphenyl)carbazol-3-yl]boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 ALTSSZFRWDVXPB-UHFFFAOYSA-N 0.000 description 4
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 229910052717 sulfur Inorganic materials 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- QAFFBUBNQSNVSZ-UHFFFAOYSA-N 2-bromo-1-iodonaphthalene Chemical compound C1=CC=CC2=C(I)C(Br)=CC=C21 QAFFBUBNQSNVSZ-UHFFFAOYSA-N 0.000 description 3
- KEWDVYIULXXMPP-UHFFFAOYSA-N 9-(2-bromophenyl)carbazole Chemical compound BrC1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 KEWDVYIULXXMPP-UHFFFAOYSA-N 0.000 description 3
- JIHNZNBRECXPJB-UHFFFAOYSA-N 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)carbazole Chemical group N=1C(N2C3=CC=CC=C3C3=CC=CC=C32)=NC(Cl)=NC=1C1=CC=CC=C1 JIHNZNBRECXPJB-UHFFFAOYSA-N 0.000 description 3
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- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 3
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- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
Description
技术领域
本发明属于有机电致发光元件用材料技术领域,具体涉及一种含磷有机化合物及其应用。
背景技术
最近几年有机电致发光显示技术己趋于成熟,一些产品已进入市场,但在产业化时程中,仍有许多问题亟待解决,特别是用于制作元件的各种有机材料,其载流子注入、传输性能,材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等,尚有许多问题还未解决。尤其是发光元件在发光效率和使用寿命还达不到实用化要求,这大大限制了OLED技术的发展。
有机电致发光主要分为荧光和磷光,但根据自旋量子统计理论,单重态激子和三重态激子的概率为1:3,即来自单重态激子辐射跃迁的荧光的理论极限为25%,三重态激子辐射跃迁的荧光的理论极限为75%。如何利用75%的三线态激子的能量成为当务之急。1997年Forrest等发现磷光电致发光现象突破了有机电致发光材料量子效率25%效率的限制,引起人们对金属配合物磷光材料的广泛关注。从此,人们对磷光材料进行大量的研究。
鉴于以上原因,特提出本发明。
发明内容
为了解决现有技术存在的以上问题,本发明提供了一种新型的含磷有机化合物,本发明的含磷有机化合物作为有机电致发光元件用材料的原料,能够提供启动电压降低、发光效率高、亮度提高的有机电致发光元件用材料以及有机电致发光元件。
为了实现上述目的,本发明采用如下技术方案:
一种含磷有机化合物,所述含磷有机化合物的结构如式(I)所示:
其中,W1~W4相同或不同地代表N或CR2,或者任意两个相邻的基团W1、W2、W3、W4代表下式(II)的基团,
其中,Z在每次出现时相同或不同地代表CR3或N,并且^指示式I中的相应的相邻基团W1和W2、W2和W3,或W3和W4;
T表示O、S、NAr3或CR4R5;
R1~R8相同或者不同,选自氢、氘、具有C1~C40的直链烷基、具有C1~C40的直链杂烷基、具有C3~C40的支链或环状的烷基、具有C3~C40的支链或环状的杂烷基、具有C2~C40的烯基或炔基、具有5~60个碳原子的芳香族环系或杂芳族环系中的一种,R1~R8中的每个基团可被一个或多个基团R取代,且其中两个或更多个相邻的取代基团可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系;
Ar1、Ar2、Ar3相同或者不同,选自具有C1~C40的直链烷基、具有C1~C40的直链杂烷基、具有C3~C40的支链或环状的烷基、具有C3~C40的支链或环状的杂烷基、具有C2~C40的烯基或炔基、具有5~60个碳原子的芳香族环系或杂芳族环系,所述环系可被一个或多个基团R取代;
所述R每次出现时相同或不同,选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar4)2、N(R9)2、C(=O)Ar4、C(=O)R9、P(=O)(Ar4)2、具有C1~C40的直链烷基、具有C1~C40的直链杂烷基、具有C3~C40的支链或环状的烷基、具有C3~C40的支链或环状的杂烷基、具有C2~C40的烯基或炔基、具有5~80个碳原子的芳族环或杂芳族环系、具有5~60个碳原子的芳氧基或杂芳氧基中的一种,R基团中的每个基团可被一个或多个基团R9取代,或这些体系的组合,其中一个或多个非相邻的-CH2-基团可被R9C=CR9、C≡C、Si(R9)2、Ge(R9)2、Sn(R9)2、C=O、C=S、C=Se、C=NR9、P(=O)(R9)、SO、SO2、NR9、O、S或CONR9代替,并且其中一个或多个氢原子或被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R9取代;
R9每次出现时相同或不同,选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar4)2、N(R10)2、C(=O)Ar4、C(=O)R10、P(=O)(Ar4)2、具有C1~C40的直链烷基、具有C1~C40的直链杂烷基、具有C3~C40的支链或环状的烷基、具有C3~C40的支链或环状的杂烷基、具有C2~C40的烯基或炔基、具有5~60个碳原子的芳族环或杂芳族环系、具有5~60个碳原子的芳氧基或杂芳氧基中的一种,R9中的每个基团可被一个或多个基团R10取代,或这些体系的组合,其中一个或多个非相邻的-CH2-基团可被R10C=CR10、C≡C、Si(R10)2、Ge(R10)2、Sn(R10)2、C=O、C=S、C=Se、C=NR10、P(=O)(R10)、SO、SO2、NR10、O、S或CONR10代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R10取代;
Ar4在每次出现时相同或不同,选自具有5~30个碳原子的芳族或杂芳族环系,所述环系可被一个或多个非芳族基团R10取代;此处键合至同一氮原子或磷原子的两个基团Ar4也可通过单键或选自N(R10)、C(R10)2、氧或硫的桥连基彼此桥连;
R10选自氢原子、氘原子、氟原子、腈基、具有C1~C20的脂族烃基、具有5~30个碳原子的芳族环或杂芳族环系,其中R10中一个或多个氢原子可被氘原子、卤素原子、或腈基代替,其中两个或更多个相邻的取代基R10可彼此形成单环或多环的脂族、芳族或杂芳族环系。
在本发明意义上的芳族或杂芳族环系旨在被认为是指不必仅含有芳基或杂芳基的体系,而是其中多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接。因此,例如,和其中两个或更多个芳基被例如短的烷基连接的体系一样,诸如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的体系也被认为是指在本发明意义上的芳族环系。
本发明意义上的芳基含有5~60个碳原子,在本发明意义上的杂芳基含有5~60个碳原子和至少一个杂原子,其条件是碳原子和杂原子的总和至少是5;所述杂原子优选选自N、O或S。此处的芳基或杂芳基被认为是指简单的芳族环,即苯、萘等,或简单的杂芳族环,如吡啶、嘧啶、噻吩等,或稠合的芳基或杂芳基,如蒽、菲、喹啉、异喹啉等。通过单键彼此连接的芳族环,例如联苯,相反地不被称为芳基或杂芳基,而是称为芳族环系。
对于本发明意义上的含有1~40个碳原子并且其中单独的氢原子或-CH2-基团还可被上述基团取代的脂族烃基或者烷基或者烯基或炔基优选被认为是指如下基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。烷氧基优选具有1~40个碳原子的烷氧基被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。杂烷基优选具有1~40个碳原子的烷基,是指其中单独的氢原子或-CH2-基团可被氧、硫、卤素原子取代的基团,被认为是指烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基,特别是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
一般来说,根据本发明的环烷基、环烯基可为环丙基、环丁基、环戊基、环己基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基,其中一个或多个-CH2-基团可被上述基团代替;此外,一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
根据本发明的芳族或杂芳族环原子,在每种情况下还可被上述基团R10取代的芳族或杂芳族环系,特别是指衍生自如下物质的基团:苯、萘、蒽、苯并蒽、菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘,4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。
进一步的,所述式(I)主要包括以下式(I)-1~式(I)-7所示的结构:
进一步的,所述R1~R8相同或者不同,选自氢、氘、具有5~60个碳原子的芳香族环系或杂芳族环系中的一种,所述R1~R8中的每个基团可被一个或多个基团R取代,且其中两个或更多个相邻的取代基团可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系;
所述Ar1、Ar2、Ar3选自具有5~60个碳原子的芳香族环系或杂芳族环系,所述环系可被一个或多个基团R取代。
进一步的,所述含磷有机化合物主要包括如下PP017~PP280所示化合物:
一种所述的含磷有机化合物在有机元件用材料中的应用。
进一步的,所述有机元件用材料为有机电致发光元件用材料、有机场效应晶体管用材料或有机薄膜太阳能电池用材料。
进一步的,所述含磷有机化合物在发光层材料、电子输送/空穴阻挡层材料或封装层材料中的应用。
一种有机电致发光元件,包括第一电极、第二电极和位于第一电极和第二电极之间的多层有机层,所述有机层中的至少一层包含所述的含磷有机化合物。
所述有机电致发光元件包含阴极、阳极和至少一个发光层。除了这些层之外,它还可以包含其它的层,例如在每种情况下,包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而,应当指出,这些层中的每个并非必须都存在。此处所述有机电致发光装置可包含一个发光层,或者它可包含多个发光层。即,将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系,其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层,则根据本发明,这些层中的至少一个层包含本发明的含磷有机化合物。
在根据本发明的有机电致发光元件的其它层中,特别是在电子传输层中以及在空穴阻挡层和薄膜封装层中,所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。
此外优选如下的有机电致发光元件,借助于升华方法施加一个或多个层,其中在真空升华装置中在低于10-5Pa、优选低于10-6Pa的初压下通过气相沉积来施加所述材料。然而,所述初压还可能甚至更低,例如低于10-7Pa。
同样优选如下的有机电致发光元件,借助于有机气相沉积方法或借助于载气升华来施加一个或多个层,其中,在10-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸气喷印方法,其中所述材料通过喷嘴直接施加,并且因此是结构化的。
此外优选如下的有机电致发光元件,从溶液中,例如通过旋涂,或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷,来产生一个或多个层。可溶性化合物,例如通过适当的取代式(I)所示的化合物获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法,其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。
进一步地,所述有机层还包括选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层、发光层、光折射层的一种以上。
本发明的有机电致发光元件既可以是顶发射光元件,又可以是底发射光元件。本发明的有机电致发光元件的结构和制备方法没有限定。采用本发明的化合物制得的有机电致发光元件可降低启动电压、提高发光效率和亮度。
一种显示装置,包括所述的有机电致发光元件。
一种照明装置,包括所述的有机电致发光元件。
本发明的有机元件用材料含有本发明的含磷有机化合物。有机元件用材料可以单独使用本发明的化合物构成,也可以同时含有其他化合物。
本发明的有机电致发光元件用材料中所含有的本发明的含磷有机化合物可以用作主体材料,此时,本发明的有机电致发光元件用材料中可以含有作为掺杂材料的其他化合物。
本发明的有机电致发光元件用材料还可以作为空穴传输层、增强层、发光层、电子传输层、电荷产生层、电子阻挡层、封装层或光折射层用材料。
与现有技术相比,本发明的有益效果为:本发明所述的含磷有机化合物具有较高的三重态能级、高的玻璃化温度,适宜作为有机电致发光元件用材料使用,含有所述的含磷有机化合物的有机电致发光元件用材料,具有启动电压低,发光效率和亮度高的特点。另外,本发明的含磷有机化合物具有良好的热稳定性和成膜性能,应用在有机电致发光元件用材料、有机电致发光元件、显示装置、照明装置中,能够延长使用寿命,从而能够降低有机电致发光元件用材料、有机电致发光元件、显示装置、照明装置的制造成本。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的一些实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1是本发明的有机电致发光装置的一个底部发光例子的示意图;
图2是本发明的有机电致发光装置的一个顶部发光例子的示意图。
附图标记
1-基板、2-阳极、3-空穴注入层、4-空穴传输/电子阻挡层、5-发光层、6-空穴阻挡/电子传输层、7-电子注入层、8-阴极。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚,下面将对本发明的技术方案进行详细的描述。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,不应视为对本发明的具体限制。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动的前提下所得到的所有其它实施方式,都属于本发明所保护的范围。
以下实施例中OLED材料及元件进行性能测试的测试仪器及方法如下:
OLED元件性能检测条件:
亮度和色度坐标:使用光谱扫描仪PhotoResearchPR-715测试;
电流密度和起亮电压:使用数字源表Keithley2420测试;
功率效率:使用NEWPORT1931-C测试;
寿命测试:使用LTS-1004AC寿命测试装置。
本发明式(I)所示的化合物(I)-7的代表合成方法如下:
其中,X为卤素,具体可选自氯、溴或碘。
上述第三步反应为常见的卤代反应,第四步反应为常见的Suzuki或者Buchwald-Hartwig偶联反应,根据Ar1和Ar2的具体结构不同,可以选择不同的原材料,具体可参见下文的合成例。
具体的,针对本发明式(I)所示的化合物(I)-1~(I)-6的制备可以选择下述特定的合成方法:
其中,X1、X2为卤素或磺酸酯,具体可选自氯、溴、碘或OTf。
实施例1
化合物PP020的合成,包括如下步骤:
第一步:化合物Int-1的制备
在氮气保护下,0.10mol的9-(2-溴苯基)-9H-咔唑溶解于200mL干燥的THF中,液氮降温至-78℃,滴加入44mL的2.5M正丁基锂正己烷溶液,搅拌反应30分钟,滴加入0.12mol的苯基二氯化磷(CAS:644-97-3),升至室温搅拌反应2小时,滴加入100mL的冰水,分出有机相,水相用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物Int-1,白色固体,收率65%。
第二步:化合物Int-2的制备
0.10mol第一步制备的中间体Int-1溶解在200mL的乙腈中,加入0.01mol的硝酸银,升温至90℃搅拌反应3小时,冷却到室温,减压浓缩干,用硅胶柱分离纯化,得到白色固体产物Int-2,收率84%。
第三步:化合物Int-3的制备
50.0mmol第二步制备的中间体Int-2溶解在100mL的冰醋酸中,加入22.0mmol的碘酸钾和33.0mmol的碘化钾,升温回流搅拌反应3小时,冷却到室温,过滤,滤饼用水洗、碳酸钠水溶液洗、水洗,得到中间体Int-3,白色固体,收率92%。
第四步:化合物PP020的制备
20.0mmol中间体Int-3溶解于60mL的甲苯中,在氮气保护下,加入24.0mmol的(9-([1,1'-联苯]-3-基)-9H-咔唑-3-基)硼酸(CAS:1416814-68-0)、80.0mmol的无水碳酸钠、0.1mmol的Pd(PPh3)4催化剂和30mL的乙醇以及30mL的水,升温回流搅拌反应5小时,冷却到室温,加入50mL水稀释,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到产物PP020,白色固体,收率86%。
实施例2
化合物PP017的制备,参照实施例1的合成方法,仅将实施例1第四步的(9-([1,1'-联苯]-3-基)-9H-咔唑-3-基)硼酸替换为N-苯基-3-咔唑硼酸(CAS:854952-58-2),制备化合物PP017,收率90%。
实施例3
化合物PP018、PP019、PP021~PP034、PP047~PP082的制备,参照实施例1的合成方法,仅将实施例1第四步的(9-([1,1'-联苯]-3-基)-9H-咔唑-3-基)硼酸替换为相应的芳基硼酸,制备化合物PP018、PP019、PP021~PP034、PP047~PP082。
实施例4
化合物PP039的制备:
第一步:化合物Int-4的制备
0.10mol的中间体Int-3、0.12mol的联二硼酸频那醇酯溶解于80mL的DMF中,在氮气保护下,加入0.15mol的无水醋酸钾和1.0mmol的PdCl2(dppf)催化剂,升温至90℃搅拌反应8小时,冷却到室温,加入200mL水稀释,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物Int-4,白色固体,收率92%。
第二步:化合物PP039的制备
20.0mmol的中间体Int-4溶解于60mL的甲苯中,在氮气保护下,加入18.0mmol的2-氯-4-(二苯并[b,d]呋喃-1-基)-6-苯基-1,3,5-三嗪(CAS:1883265-32-4)、80.0mmol的无水碳酸钾、0.2mmol的Pd(PPh3)4催化剂和30mL的乙醇以及30mL的水,升温回流搅拌反应10小时,冷却到室温,加入100mL甲苯和50.0mmol的水,分出有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到产物PP039,白色固体,收率78%。
实施例5
化合物PP035~PP038、PP040~PP046的制备,参照实施例4的合成方法,仅将实施例4第二步的2-氯-4-(二苯并[b,d]呋喃-1-基)-6-苯基-1,3,5-三嗪替换为相应的卤代物,制备化合物PP035~PP038、PP040~PP046。
实施例6
化合物PP113的合成,包括如下步骤:
第一步:化合物Int-5的制备
在氮气保护下,0.10mol的咔唑、0.12mol的2-溴-1-碘萘溶解于150mL干燥的二甲苯中,再加入0.20mol的无水碳酸钾、10.0mmol的碘化亚铜和20.0mmol的DMEDA,升温回流搅拌反应12小时,冷却到室温,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物Int-5,黄色固体,收率93%。
第二步:化合物Int-6的制备
参照实施例1中第一步的制备方法,仅将实施例1中第一步的9-(2-溴苯基)-9H-咔唑替换为上步制备的中间体Int-5,制备中间体Int-6,白色固体,收率62%。
第三步:化合物Int-7的制备
参照实施例1中第二步的制备方法,仅将实施例1中第二步的Int-1替换为上步制备的中间体Int-6,制备中间体Int-7,白色固体,收率80%。
第四步:化合物Int-8的制备
参照实施例1中第三步的制备方法,仅将实施例1中第三步的Int-2替换为上步制备的中间体Int-7,制备中间体Int-8,白色固体,收率94%。
第五步:化合物PP113的制备
参照实施例1中第四步的制备方法,将实施例1中第四步的Int-3替换为上步制备的中间体Int-8,将实施例1中第四步的(9-([1,1'-联苯]-3-基)-9H-咔唑-3-基)硼酸替换为(9-(苯并菲-2-基)-9H-咔唑-3-基)硼酸(CAS:1872269-04-9)制备化合物PP113,白色固体,收率88%。
实施例7
化合物PP083~PP090、PP095~PP112、PP114~PP120、PP129~PP141的制备,参照实施例6的合成方法,将实施例6第一步的2-溴-1-碘萘替换为2-碘-1-溴萘(CAS:90948-03-1),或者仅将实施例6第五步的(9-(苯并菲-2-基)-9H-咔唑-3-基)硼酸替换为相应的芳基硼酸,制备化合物PP083~PP090、PP095~PP112、PP114~PP120、PP129~PP141。
实施例8
化合物PP128的制备:
第一步:化合物Int-9的制备
参照实施例4中第一步的制备方法,仅将实施例4中第一步的Int-3替换为中间体Int-8,制备中间体Int-9,白色固体,收率89%。
第二步:化合物PP128的制备
参照实施例4中第二步的制备方法,仅将实施例4中第二步的Int-4替换为中间体Int-9,将2-氯-4-(二苯并[b,d]呋喃-1-基)-6-苯基-1,3,5-三嗪替换为9-(4-氯-6-苯基-1,3,5-三嗪-2-基)-9H-咔唑(CAS:1268244-56-9)制备化合物PP128,白色固体,收率76%。
实施例9
化合物PP91~PP94、PP121~PP127的制备,参照实施例8的合成方法,仅将实施例8第二步的9-(4-氯-6-苯基-1,3,5-三嗪-2-基)-9H-咔唑替换为相应的卤代物,制备化合物PP91~PP94、PP121~PP127。
实施例10
中间体A的制备:
第一步:化合物Int-10的制备
参照实施例6中第一步的制备方法,仅将实施例6中第一步的2-溴-1-碘萘替换为3-溴-4-碘二苯并呋喃,将实施例6中第一步的咔唑替换为3-氯咔唑,制备中间体Int-10,白色固体,收率75%。
第二步:化合物Int-11的制备
参照实施例1中第一步的制备方法,仅将实施例1中第一步的9-(2-溴苯基)-9H-咔唑替换为上步制备的中间体Int-10,制备中间体Int-11,白色固体,收率65%。
第三步:中间体A1的制备
参照实施例1中第二步的制备方法,仅将实施例1中第二步的Int-1替换为上步制备的中间体Int-11,制备中间体A1,浅黄色固体,收率82%。
以上述类似的合成方法,制备以下中间体:
实施例11
化合物PP259的制备:
20.0mmol的中间体A1溶解于60mL的甲苯中,在氮气保护下,加入22.0mmol的(4-(9H-咔唑-9-基)萘-1-基)硼酸(CAS:1246021-50-0)、80.0mmol的磷酸钾、0.1mmol的Pd132催化剂和30mL的乙醇以及30mL的水,升温回流搅拌反应10小时,冷却到室温,加入100mL甲苯和50.0mmol的水,分出有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到产物PP259,白色固体,收率82%。
实施例12
化合物PP239~PP247、PP253~PP258、PP260的制备,参照实施例11的合成方法,仅将实施例11中的(4-(9H-咔唑-9-基)萘-1-基)硼酸替换为相应的有机硼酸或硼酸频那醇酯,制备化合物PP239~PP247、PP253~PP258、PP260。
实施例13
中间体B1的制备:
参照实施例4中第一步的制备方法,仅将实施例4中第一步的Int-3替换为中间体A1,制备中间体B1,白色固体,收率79%。
以上述类似的合成方法,制备以下中间体:
实施例14
化合物PP252的制备:
20.0mmol的中间体B1溶解于60mL的甲苯中,在氮气保护下,加入17.0mmol的2-氯-4-(二苯并[b,d]呋喃-4-基)-6-苯基-1,3,5-三嗪(CAS:1472729-25-1)、80.0mmol的磷酸钾、0.1mmol的Pd132催化剂和30mL的乙醇以及30mL的水,升温回流搅拌反应10小时,冷却到室温,加入50mL甲苯和50.0mmol的水,分出有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到产物PP252,白色固体,收率74%。
实施例15
化合物PP248~PP251的制备,参照实施例14的合成方法,仅将实施例14中的2-氯-4-(二苯并[b,d]呋喃-4-基)-6-苯基-1,3,5-三嗪替换为相应的卤代物,制备化合物PP248~PP251。
实施例16
化合物PP142的制备:
参照实施例11的合成方法,仅将实施例11中的A1替换为A16,将(4-(9H-咔唑-9-基)萘-1-基)硼酸替换为二苯并呋喃-2-硼酸(CAS:402936-15-6),制备化合物PP142,白色固体,收率83%。
实施例17
化合物PP143~PP152、PP161~PP169的制备,参照实施例16的合成方法,仅将实施例16中的二苯并呋喃-2-硼酸替换为相应的有机硼酸或硼酸频那醇酯,制备化合物PP143~PP152、PP161~PP169。
实施例18
化合物PP153~PP155的制备,参照实施例14的合成方法,仅将实施例14中的2-氯-4-(二苯并[b,d]呋喃-4-基)-6-苯基-1,3,5-三嗪替换为相应的卤代物,将实施例14中的B1替换为B16,制备化合物PP153~PP155。
实施例19
化合物PP160的制备:
20.0mmol的中间体A16溶解于80mL的甲苯中,在氮气保护下,加入18.0mmol的5-(2-萘基)-5,10-二氢吩嗪(CAS:1225066-62-5)、27.0mmol的叔丁醇钠、0.09mmol的Pd2(dba)3催化剂和0.02mL的10%三叔丁基磷甲苯溶液以及0.2mmol的碘化亚铜,升温至100℃搅拌反应10小时,冷却到室温,加入50.0mmol的水,过滤,滤饼用水洗,用硅胶柱分离纯化,得到产物PP160,白色固体,收率87%。
实施例20
化合物PP156~PP159的制备,参照实施例19的合成方法,仅将实施例19中的5-(2-萘基)-5,10-二氢吩嗪替换为相应的胺基反应物,制备化合物PP156~PP159。
实施例21
化合物PP261~PP267、PP273~PP280的制备,参照实施例11的合成方法,仅将实施例11中的A1替换为A4,将(4-(9H-咔唑-9-基)萘-1-基)硼酸替换为相应的硼酸或硼酸频那醇酯,制备化合物PP261~PP267、PP273~PP280。
实施例22
化合物PP268~PP272的制备,参照实施例14的合成方法,仅将实施例14中的2-氯-4-(二苯并[b,d]呋喃-4-基)-6-苯基-1,3,5-三嗪替换为相应的卤代物,将实施例14中的B1替换为B4,制备化合物PP268~PP272。
实施例23
化合物PP170~PP180、PP186~PP194的制备,参照实施例11的合成方法,仅将实施例11中的A1替换为A13,将(4-(9H-咔唑-9-基)萘-1-基)硼酸替换为相应的硼酸或硼酸频那醇酯,制备化合物PP170~PP180、PP186~PP194。
实施例24
化合物PP181~PP185的制备,参照实施例14的合成方法,仅将实施例14中的2-氯-4-(二苯并[b,d]呋喃-4-基)-6-苯基-1,3,5-三嗪替换为相应的卤代物,将实施例14中的B1替换为B13,制备化合物PP181~PP185。
实施例25
化合物PP195~PP200、PP207~PP216的制备,参照实施例11的合成方法,仅将实施例11中的A1替换为A10,将(4-(9H-咔唑-9-基)萘-1-基)硼酸替换为相应的硼酸或硼酸频那醇酯,制备化合物PP195~PP200、PP207~PP216。
实施例26
化合物PP201~PP206的制备,参照实施例14的合成方法,仅将实施例14中的2-氯-4-(二苯并[b,d]呋喃-4-基)-6-苯基-1,3,5-三嗪替换为相应的卤代物,将实施例14中的B1替换为B10,制备化合物PP201~PP206。
实施例27
化合物PP217~PP228、PP234~PP238的制备,参照实施例11的合成方法,仅将实施例11中的A1替换为A7,将(4-(9H-咔唑-9-基)萘-1-基)硼酸替换为相应的硼酸或硼酸频那醇酯,制备化合物PP217~PP228、PP234~PP238。
实施例28
化合物PP229~PP233的制备,参照实施例14的合成方法,仅将实施例14中的2-氯-4-(二苯并[b,d]呋喃-4-基)-6-苯基-1,3,5-三嗪替换为相应的卤代物,将实施例14中的B1替换为B7,制备化合物PP229~PP233。
有机电致发光元件的制备
对比例1
将下述的化合物A1和A2的混合物作为绿光主体材料,其中A1和A2的质量比为11:9,使用下述的化合物B作为绿光掺杂材料,化合物C作为孔穴注入材料,化合物D作为空穴传输材料、化合物E作为红光材料,化合物F作为红光掺杂材料,化合物G作为电子传输掺杂材料,LiQ作为电子传输主体材料。
试验例1
将化合物A替换为本发明的化合物PP017~PP280,按照对比例1的方法制备绿光有机电致发光元件。
所得绿光有机电致发光元件的性能检测结果列于表1中,其中驱动电压(V)、电流效率(LE)、色坐标(CIE)、半峰宽(FWHM)是在元件的电流密度为10mA/cm2条件下得出,且电压、LE、FWHM和LT90%相较参比元件进行了数据归一化处理。
表1绿光元件性能检测结果
由表1可知,本发明的有机材料制备成的绿光元件相较于对比例1制备的元件,驱动电压低,电流效率较高,色纯度好,而且在元件发光亮度初始为2000cd/cm2为初始的条件下,使用本发明的化合物作为绿光主体材料的元件寿命有很大提高。
表1中仅列举了部分的PP017~PP280中部分化合物的性能,其他化合物性能与表中列举的化合物的结构基本一致,由于篇幅有限,不再一一列举。
按照对比例1的方法制备红光元件,其中,将前述的化合物E替换为本发明的化合物PP017~PP280,除此之外,ITO/C/D/[本发明的化合物PP017~PP280]+F(3%)/LiQ+G(50%)/LiF/Al(2nm)。
所得元件的性能检测结果列于表2中,其中驱动电压(V)、电流效率(LE)、色坐标(CIE)、半峰宽(FWHM)是在元件的电流密度为10mA/cm2条件下得出,且电压、LE、FWHM和LT90%相较参比元件进行了数据归一化处理。
表2红光元件性能检测结果
由表2的红光元件性能测试结果可知,本发明的有机材料制备成的元件相较于对比例1制备的红光元件驱动电压明显降低,电流效率高,发光色纯度好。在元件初始亮度为2000cd/cm2为初始的条件下,使用本发明的化合物作为红光主体材料的元件LT90%寿命有显明的提高。
表2中仅列举了部分的PP017~PP280中部分化合物的性能,其他化合物性能与表中列举的化合物的结构基本一致,由于篇幅有限,不再一一列举。
如图1和2所示,分别为本发明的有机电致发光装置的一个底部发光例子的示意图和有机电致发光装置的一个顶部发光例子的示意图,本发明制备的含磷有机化合物包含在发光层5中。
以上所述,仅为本发明的具体实施方式,但本发明的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明揭露的技术范围内,可轻易想到变化或替换,都应涵盖在本发明的保护范围之内。因此,本发明的保护范围应以所述权利要求的保护范围为准。
Claims (7)
2.一种权利要求1所述的含磷有机化合物在有机元件用材料中的应用。
3.根据权利要求2所述的应用,其特征在于,所述有机元件用材料为有机电致发光元件用材料、有机场效应晶体管用材料或有机薄膜太阳能电池用材料。
4.根据权利要求2所述的应用,其特征在于,所述含磷有机化合物在发光层材料、电子输送/空穴阻挡层材料或封装层材料中的应用。
5.一种有机电致发光元件,其特征在于,包括第一电极、第二电极和位于第一电极和第二电极之间的多层有机层,所述有机层中的至少一层包含权利要求1所述的含磷有机化合物。
6.一种显示装置,其特征在于,包括权利要求5所述的有机电致发光元件。
7.一种照明装置,其特征在于,包括权利要求5所述的有机电致发光元件。
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