WO2024055196A1 - 一种a-d-a型有机化合物及其制备方法 - Google Patents

一种a-d-a型有机化合物及其制备方法 Download PDF

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WO2024055196A1
WO2024055196A1 PCT/CN2022/118717 CN2022118717W WO2024055196A1 WO 2024055196 A1 WO2024055196 A1 WO 2024055196A1 CN 2022118717 W CN2022118717 W CN 2022118717W WO 2024055196 A1 WO2024055196 A1 WO 2024055196A1
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organic compound
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唐建新
谢凤鸣
李昊泽
李艳青
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苏州大学
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
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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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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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

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  • the invention relates to a luminescent material with an A-D-A structure, the application of such compounds, and an organic electroluminescent device using such compounds.
  • organic materials In order to improve the efficiency of organic light-emitting diodes, various types of organic materials have been developed, such as traditional fluorescent materials, heavy metal-based phosphorescent materials, organic thermally activated delayed fluorescent materials, host materials, hole transport materials, electron transport materials, etc. Fluorescent materials have good reliability, but low efficiency. Phosphorescent materials are highly efficient, but require the use of heavy metals and are expensive. Thermal-activated delayed fluorescent materials are not only highly efficient, but also pure organic compounds. However, the device efficiency has a significant roll-off, which limits its application under high brightness. It is crucial to develop new, efficient organic light-emitting materials that can be used in the OLED field.
  • the object of the present invention is to provide a thermally activated delayed fluorescent material with an A-D-A type, which can be used in electroluminescent devices.
  • the invention relates to a new type of luminescent material and a preparation method thereof.
  • the luminescent material has thermally activated delayed fluorescence properties.
  • the single molecule structure presents a face-to-face arrangement in space. It has excellent luminescent properties and can be used as an organic electroluminescent device.
  • Light-emitting layer materials that can achieve high efficiency and low roll-off at the same time will bring huge application prospects and economic value.
  • the ADA type organic compound of the present invention is represented by the following general formula: .
  • R′ and R′′ are selected from one of the following substituted or unsubstituted groups: C1 to C10 alkyl, C6 to C30 monocyclic aromatic hydrocarbons or condensed ring aromatic hydrocarbons, C5 ⁇ C30 monocyclic heteroaromatic hydrocarbons or condensed ring heteroaromatic hydrocarbons.
  • the substituent is selected from one of deuterium, trifluoromethyl, cyano group, halogen, C1-C10 alkyl or cycloalkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group.
  • Heteroatoms in the present invention generally refer to atoms or atomic groups selected from N, O, S, P, Si and Se, with N, O and S being preferred.
  • the invention discloses a preparation method of the above-mentioned A-D-A type organic compound, which is obtained by reacting raw material one and raw material two; the reaction is carried out in the presence of lithium reagent and acid; the preferred lithium reagent is n-butyllithium; the acid has a concentration of 30% ⁇ 37% concentrated hydrochloric acid and acetic acid; the reaction is a continuous one-pot method for closed-loop reaction. Specifically, in a nitrogen atmosphere, raw material 1 is subjected to a metallization reaction through a lithium compound, then raw material 2 is added to perform a coupling reaction, and finally the ring-closing reaction is completed under acidic conditions.
  • the chemical structural formula of the second raw material is as follows: .
  • the compound described in the general formula of the present invention can preferably be one of the following specific compounds, and these compounds are only representative.
  • the invention discloses the application of the above-mentioned A-D-A type organic compound in preparing organic electroluminescent devices.
  • a luminescent layer material it is preferably used as a luminescent dye and/or sensitizer.
  • the OLED device prepared by using the compound of the present invention has low turn-on voltage, high luminous efficiency, high color purity and better service life.
  • the preparation process of the compound of the present invention is simple and easy to implement, the raw materials are easily available, and it is suitable for mass production and scale-up.
  • Figure 1 is a hydrogen spectrum of compound 2PXZ2TRZ prepared in the embodiment of the present invention.
  • Figure 2 is the mass spectrum of compound 2PXZ2TRZ prepared in the embodiment of the present invention.
  • Figure 3 is a device efficiency diagram of device D1 prepared in an embodiment of the present invention.
  • Figure 4 is an electroluminescence spectrum chart of the device D1 prepared in the embodiment of the present invention.
  • n-butyllithium (2.0 M, 3.00 ml) was added dropwise to a low-temperature (-78°C) solution of raw material A1 (1.00g, 1.67 mmol) in tetrahydrofuran, and stirred at -78°C for 1 hour.
  • raw material B1 (2.40 g, 4.92 mmol) dissolved in tetrahydrofuran solution, then stir at room temperature for 12 hours, then remove the solvent under reduced pressure, then add acetic acid (40 ml) and hydrochloric acid (36%, 1 ml), at 120
  • the reaction was carried out for 15 hours at °C. After the reaction was completed, the reaction solution was poured into water and filtered under reduced pressure.
  • Figure 1 is the hydrogen spectrum of compound 2PXZ2TRZ;
  • Figure 2 is the mass spectrum of compound 2PXZ2TRZ.
  • the by-product 2PXZTRZ (0.35 g, yield: 21%) was also obtained as a white powder.
  • MALDI-TOF-MS result molecular ion peak 988.945.
  • the invention discloses that the above compound is used as a guest material doped with a host material as a luminescent layer, or directly as a luminescent layer, for preparing an organic electroluminescent device; further, when the above compound is used as a guest material and doped with a host material to jointly serve as a luminescent layer,
  • the doping concentration of the compound is 20 wt%. Doping concentration refers to the percentage of the guest material that accounts for the mass sum of the guest material and the host material.
  • ITO indium tin oxide
  • HIL hole injection layer
  • TAPC 4,4'-(cyclohexane-1,1-diyl)bis(N,N -Di-p-tolylaniline)
  • HTL hole transport layer
  • TCTA 4,4′,4′′-tris(carbazol-9-yl)triphenylamine
  • EBL electron blocking layer
  • EBL electron blocking layer
  • the specific performance data of the organic electroluminescent device based on the compounds prepared in the above embodiments are detailed in Table 1.
  • the specific testing method is based on the existing technology.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

本发明涉及一种A-D-A型有机化合物及其制备方法，该材料具有热激活延迟荧光性质，单分子结构在空间上呈现一种面对面的受体-供体-受体（A-D-A）排列，该类化合物主要功能是通过空间非共轭连接来实现分子内相互作用，双重空间相互作用使该类材料具有优异的发光性能，可以用作有机发光器件的有机材料层的材料，特别是发光材料和/或敏化剂。

Description

一种A-D-A型有机化合物及其制备方法 技术领域
本发明涉及一种具有A-D-A型结构的发光材料，同时还涉及该类化合物的应用，以及涉及采用该类化合物有机电致发光器件。
 背景技术
为了提高有机发光二极管的效率，各类有机材料已被开发出来，如传统荧光材料、基于重金属的磷光材料、有机热激活延迟荧光材料、主体材料、空穴传输材料、电子传输材料等。荧光材料的可靠性好，但是效率低。磷光材料效率高，但需要使用重金属，价格昂贵。热激活延迟荧光材料不仅效率高，而且是纯有机化合物，但是器件效率滚降明显，限制了其在高亮度下的应用。开发新型的、高效的、可用于OLED领域的有机发光材料至关重要。
 技术问题
为了解决上述技术问题，本发明的目的在于提供一种具有A-D-A型的热激活延迟荧光材料，可用于电致发光器件。本发明涉及一种新型发光材料及其制备方法，该发光材料具有热激活延迟荧光性质，单分子结构在空间上呈现一种面对面的排列，具有优异的发光性能，可以用作有机电致发光器件的发光层材料，同时能够实现高效率低滚降的发光器件，将会带来巨大的应用前景和经济价值。
 技术解决方案
本发明的A-D-A型有机化合物由如下通式所示： 。
式中： R 1、R 2、R 3和R 4独立的选自下述基团中的一种：氢、甲基、叔丁基、环己烷基、苯基、4-叔丁基苯基、二苯胺基、含氮芳环（比如咔唑基等）；X 1和/或X 2未取代，或者，X 1、X 2独立的选自单键、双键、O、S、S(＝O) 2、CR′R″或Se；X 1和/或X 2未取代是指X 1和/或X 2不存在；A选自C6～C60的芳胺或杂芳基。
进一步的，CR′R″中，R′和R″选自取代或未取代的下述基团中的一种：C1～C10的烷基、C6～C30的单环芳烃或稠环芳烃、C5～C30的单环杂芳烃或稠环杂芳烃。优选的，取代基选自氘、三氟甲基、氰基、卤素、C1-C10的烷基或环烷基、C6-C30的芳基、C3-C30的杂芳基中的一种。
本发明中的杂原子，通常指选自N、O、S、P、Si和Se中的原子或原子团，优选N、O和S。
本发明公开了上述A-D-A型有机化合物的制备方法，由原料一与原料二反应得到；所述反应在锂试剂、酸存在下进行；优选的锂试剂为正丁基锂；酸为浓度30%~37%的浓盐酸、醋酸；反应为连续一锅法进行闭环反应。具体的，在氮气气氛下，以原料一经过锂化合物进行金属化反应，然后加入原料二进行偶联反应，最后在酸性条件下完成闭环反应。
所述原料一的化学结构式如下： 。
所述原料二的化学结构式如下： 。
原料一、原料二中，取代基与上述A-D-A型有机化合物的取代基一样，Y为卤素，比如Cl，Br或I。
本发明的通式所述的化合物可以优选出下述具体化合物中的一种，这些化合物仅为代表性的。
。
本发明公开了上述A-D-A型有机化合物在制备有机电致发光器件中的应用，具体的，作为发光层材料，优选作为发光染料和/或敏化剂。
 有益效果
采用本发明化合物制备的OLED器件具有低开启电压、高发光效率、高色纯度和更优的使用寿命。
本发明化合物的制备工艺简单易行，原料易得，适合于量产放大。
 附图说明
图1为本发明实施例制备的化合物2PXZ2TRZ的氢谱。
图2为本发明实施例制备的化合物2PXZ2TRZ的质谱。
图3为本发明实施例制备的器件D1的器件效率图。
图4为本发明实施例制备的器件D1的电致发光光谱图。
 本发明的实施方式
下面将以多个合成实施例为例来详述本发明的上述新化合物的具体制备方法，但本发明的制备方法并不限于这些合成实施例。本发明所有原料都是现有产品，具体制备方以及测试方法为常规技术。本发明A-D-A型有机化合物的制备示意如下。
。
实施例一 化合物的2PXZ2TRZ合成。
。
在氮气氛围下，将正丁基锂（2.0 M，3.00毫升）滴加到原料A1（1.00克，1.67毫摩尔）的四氢呋喃低温（-78 ℃）溶液中，在-78 ℃下搅拌1小时后，加入溶于四氢呋喃溶液的原料B1（2.40克，4.92毫摩尔），然后于室温搅拌12小时，再减压除去溶剂，然后加入醋酸（40毫升）和盐酸（36%，1毫升），在120 ℃下反应15小时，反应完成后将反应液倒入水中减压抽滤，滤渣通过硅胶柱色谱法提纯（展开剂为二氯甲烷∶石油醚＝1:1，v/v），得化合物2PXZ2TRZ（1.26克，产量：55%），白色粉末，为主产物，MALDI-TOF-MS结果：分子离子峰1378.797。图1为化合物2PXZ2TRZ的氢谱；图2为化合物2PXZ2TRZ的质谱。还得到副产物2PXZTRZ（0.35克，产量：21%），白色粉末，MALDI-TOF-MS结果：分子离子峰988.945。
实施例二 化合物的2Cz2TRZ合成。
  。
在实施例一的基础上，将原料A1替换为原料A2（2.50克，5.13毫摩尔），其他条件不变，得到化合物2Cz2TRZ（1.18克，产量：50%），白色粉末。MALDI-TOF-MS结果：分子离子峰1346.48。
实施例三 化合物的2Cz2BO合成。
  。
在实施例二的基础上，将原料B1替换为原料B2（2.20克，4.91毫摩尔），其他条件不变，得到化合物2Cz2BO（1.18克，产量：53%），白色粉末。MALDI-TOF-MS结果：分子离子峰1268.40。
实施例四 化合物的2Cz2BN合成。
  。
在实施例二的基础上，将原料B1替换为原料B3（3.00克，5.04毫摩尔），其他条件不变，得到化合物2Cz2BN（1.37克，产量：50%），白色粉末。MALDI-TOF-MS结果：分子离子峰1560.52。
对比例一 化合物的2CzTRZ合成。
。
在实施例二的基础上，将原料A2替换为等物质的量的原料A3，其他条件不变，得到化合物2CzTRZ（0.85克，产量：55%），白色粉末。MALDI-TOF-MS结果：分子离子峰877.32。
本发明公开了上述化合物作为客体材料掺杂主体材料作为发光层，或者直接作为发光层，用于制备有机电致发光器件；进一步的，上述化合物作为客体材料掺杂主体材料共同作为发光层时，所述化合物的掺杂浓度为20 wt%。掺杂浓度指客体材料占客体材料与主体材料质量和的百分数。
应用实施例：基于上述化合物的有机电致发光器件，具体结构为：氧化铟锡(ITO)用作阳极、双吡嗪并[2,3-f:2',3'-h]喹喔啉-2,3,6,7,10,11-己腈(HATCN)用作空穴注入层(HIL)、4,4'-(环己烷-1,1-二基)双(N,N-二-对甲苯基苯胺)(TAPC)用作空穴传输层(HTL)、4,4′,4”-三(咔唑-9-基)三苯胺(TCTA)和3,3′-二(9H-咔唑-9-基)-1,1′-联苯（mCBP）用作电子阻挡层(EBL)、上述化合物作客体材料掺杂2,8-双(二苯基磷酰基)二苯并[B,D]呋喃(PPF)主体材料共同用作发光层(EML)、2,8-双(二苯基磷酰基)二苯并[B,D]呋喃(PPF)用作空穴阻挡层（HBL）、4,6-双(3,5-二(吡啶-3-基)苯基)-2-甲基嘧啶(TmPyPB)用作电子传输层(ETL)、八羟基喹啉锂(Liq)用作电子注入层(EIL)、铝(Al)用作阴极；有机电致发光器件各层规格为：ITO/HATCN (10 nm)/TAPC (40 nm)/TCTA (10 nm)/mCBP (8 nm)/PPF:客体材料(20 wt%) (20 nm)/PPF (8 nm)TmPyPB (40 nm)/Liq (3 nm)/Al (100 nm)。具体的制备工艺为常规技术，采用真空蒸镀法制备。
基于上述各个实施例所制备化合物的有机电致发光器件的具体性能数据详见表1，具体测试方法为现有技术。
。
以上实验数据表明，本发明提供的A-D-A型TADF材料应用到有机电致发光器件中后，在实现器件具有高发光效率和低效率滚降的良好性能的同时，还实现了电致发光器件的超高亮度。因此，本发明的这类新型化合物是性能良好的有机发光功能材料，有望推广商业化应用。图3为器件D1的器件效率图；图4为器件D1的电致发光光谱图。
尽管结合实施例对本发明进行了说明，但本发明并不局限于上述实施例，应当理解，在本发明构思的引导下，本领域技术人员可进行各种修改和改进，所有这些修改和改进都应属于本发明所附权利要求的保护范围。

Claims (10)

  1. 一种A-D-A型有机化合物，其特征在于，所述A-D-A型有机化合物的化学结构式如下所示：
    其中：R 1、R 2、R 3和R 4独立的选自下述基团中的一种：氢、甲基、叔丁基、环己烷基、苯基、4-叔丁基苯基、二苯胺基、含氮芳环；X 1和/或X 2未取代，或者，X 1、X 2独立的选自单键、双键、O、S、S(＝O) 2、CR′R″或Se；A选自C6～C60的芳胺或杂芳基。
  2. 根据权利要求1所述A-D-A型有机化合物，其特征在于，CR′R″中，R′和R″独立的选自取代或未取代的下述基团中的一种：C1～C10的烷基、C6～C30的单环芳烃或稠环芳烃、C5～C30的单环杂芳烃或稠环杂芳烃。
  3. 根据权利要求2所述A-D-A型有机化合物，其特征在于，取代基选自氘、三氟甲基、氰基、卤素、C1-C10的烷基或环烷基、C6-C30的芳基、C3-C30的杂芳基中的一种。
  4. 根据权利要求1所述A-D-A型有机化合物，其特征在于，所述A-D-A型有机化合物如下:
    。
  5. 权利要求1所述A-D-A型有机化合物的制备方法，其特征在于，由原料一与原料二反应得到；所述原料一的化学结构式如下：
    所述原料二的化学结构式如下：
    其中，取代基与权利要求1的取代基一样，Y为卤素。
  6. 根据权利要求5所述A-D-A型有机化合物的制备方法，其特征在于，所述反应在锂试剂、酸存在下进行。
  7. 根据权利要求6所述A-D-A型有机化合物的制备方法，其特征在于，锂试剂为正丁基锂；酸为浓度30%~37%的浓盐酸、醋酸；反应为连续一锅法进行闭环反应。
  8. 权利要求1所述A-D-A型有机化合物在制备有机电致发光器件中的应用。
  9. 权利要求1所述A-D-A型有机化合物作为发光材料的应用。
  10. 原料一与原料二在制备权利要求1所述A-D-A型有机化合物中的应用。
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