WO2019218360A1 - 聚集诱导蓝光材料及其制备方法、显示装置 - Google Patents

聚集诱导蓝光材料及其制备方法、显示装置 Download PDF

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WO2019218360A1
WO2019218360A1 PCT/CN2018/087544 CN2018087544W WO2019218360A1 WO 2019218360 A1 WO2019218360 A1 WO 2019218360A1 CN 2018087544 W CN2018087544 W CN 2018087544W WO 2019218360 A1 WO2019218360 A1 WO 2019218360A1
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formula
aggregation
blue light
reaction
compound
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PCT/CN2018/087544
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French (fr)
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李灵芝
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深圳市柔宇科技有限公司
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Priority to CN201880093838.6A priority Critical patent/CN112533915A/zh
Priority to PCT/CN2018/087544 priority patent/WO2019218360A1/zh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials

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  • the present invention relates to the field of display technologies, and in particular, to an aggregation-inducing blue light material, a preparation method thereof, and a display device.
  • OLED display devices have the advantages of self-luminous, wide viewing angle, high contrast, low power consumption, and extremely high reaction speed.
  • Luminescent materials in OLED devices usually undergo fluorescence quenching in concentrated solution or in agglomerated state.
  • the spectral peak position of the material is generally close to the target peak position.
  • the present invention provides an aggregation-inducing blue light material capable of emitting deep blue light and having strong fluorescence emission in an aggregated state, and the specific technical solution is as follows.
  • R 1 , R 2 , R 3 and R 4 are independently selected from one of H, —CH 3 and —C 2 H 6 ; and Ar is selected from the formula (2), (3) an aromatic amine group as shown;
  • R 5 and R 6 are independently selected from the group consisting of H, —CH 3 and —C(CH 3 ) 3 ; and R 7 and R 8 are independently selected from H and —CH 3 , One of -C(CH 3 ) 3 .
  • the R 1 , R 2 , R 3 and R 4 are all H; and the R 5 and R 6 are both -C(CH 3 ) 3 .
  • the R 1 , R 2 , R 3 and R 4 are all H; and the R 7 and R 8 are both -C(CH 3 ) 3 .
  • the invention also provides a preparation method of aggregation-inducing blue light material, comprising the following steps:
  • the first reaction is carried out by mixing 1,4-dibromo-2,5-diiodobenzene and benzene boron raw materials to obtain compound 1, which is one or two of phenylboronic acid and phenylboronic acid ester.
  • compound 1 is one or two of phenylboronic acid and phenylboronic acid ester.
  • the structure of the compound 1 is as shown in the formula (4):
  • R 1 and R 2 are independently selected from the group consisting of H, —CH 3 and —C 2 H 6 ; and Ar is selected from the group consisting of aromatic amine groups represented by formula (2) and formula (3);
  • R 5 and R 6 are independently selected from the group consisting of H, —CH 3 and —C(CH 3 ) 3 ; and R 7 and R 8 are independently selected from H and —CH 3 , One of -C(CH 3 ) 3 ;
  • a cyanobenzene boron-based raw material comprising one or more of substituted or unsubstituted 4-cyanobenzeneboronic acid and substituted or unsubstituted 4-cyanophenylboronic acid pinacol ester
  • the third reaction of the cyanobenzone-based raw material with the compound 2 is carried out to obtain an aggregation-inducing blue light material, wherein the aggregation-inducing blue light material has a molecular structure represented by the formula (1):
  • R 1 , R 2 , R 3 and R 4 are independently selected from one of H, —CH 3 and —C 2 H 6 ; and Ar is selected from the formula (2), (3) an aromatic amine group as shown;
  • R 5 and R 6 are independently selected from the group consisting of H, —CH 3 and —C(CH 3 ) 3 ; and R 7 and R 8 are independently selected from H and —CH 3 , One of -C(CH 3 ) 3 .
  • a catalyst is added to the first, second and third reactions, the catalyst comprising a palladium catalyst.
  • the palladium catalyst comprises tetrakis(triphenylphosphine)palladium.
  • the structure of the triphenylamine-based raw material is one of the formulas (6) and (7):
  • R 1 and R 2 in the formula (6) and the formula (7) are each independently selected from one of H, -CH 3 and -C 2 H 6 , and the formula (6) and the formula (7)
  • Each of Ar is selected from the group consisting of aromatic amine groups represented by formula (2) and formula (3);
  • R 5 and R 6 are independently selected from one of H, —CH 3 and —C(CH 3 ) 3 ; in the formula (3), R 7 and R 8 are independently One selected from the group consisting of H, -CH 3 and -C(CH 3 ) 3 .
  • the temperature of the first reaction is 65-80 ° C
  • the temperature of the second reaction is 65-80 ° C
  • the temperature of the third reaction is 100-120 ° C.
  • the first reaction, the second reaction, and the third reaction both occur in an oxygen-free environment.
  • the present invention also provides a display device comprising a light-emitting layer, the light-emitting layer comprising the aggregation-inducing blue light material according to any one of the above.
  • the luminescent layer further comprises a main blue luminescent material, and the mass ratio of the aggregation-inducing blue light material to the main blue luminescent material is 1-10:100.
  • the display device further includes a substrate, a thin film transistor layer disposed on the substrate, and the light emitting layer is disposed on a side of the thin film transistor layer away from the substrate.
  • the aggregation-inducing blue light material provided by the present invention is capable of emitting deep blue light having a wavelength of less than 450 nm and having strong fluorescence emission in an aggregated state.
  • FIG. 1 is a schematic view showing the position of a push electron group, a pull electron group and a tetraphenylbenzene in an aggregation-inducing blue light material according to a first embodiment of the present invention.
  • FIG. 2 is a flow chart of a method for preparing an aggregation-inducing blue light material according to a second embodiment of the present invention.
  • FIG. 3 is a schematic structural diagram of a display device according to the present invention.
  • references to "an embodiment” herein mean that a particular feature, structure, or characteristic described in connection with the embodiments can be included in at least one embodiment of the invention.
  • the appearances of the phrases in various places in the specification are not necessarily referring to the same embodiments, and are not exclusive or alternative embodiments that are mutually exclusive. Those skilled in the art will understand and implicitly understand that the embodiments described herein can be combined with other embodiments.
  • a first embodiment of the present invention provides an aggregation-inducing blue light material having a molecular structure represented by the formula (1):
  • R 1 , R 2 , R 3 and R 4 are independently selected from one of H, —CH 3 and —C 2 H 6 ; and Ar is selected from the formula (2), (3) an aromatic amine group as shown;
  • R 5 and R 6 are independently selected from the group consisting of H, —CH 3 and —C(CH 3 ) 3 ; and R 7 and R 8 are independently selected from H and —CH 3 , One of -C(CH 3 ) 3 .
  • the molecular structure shown by the formula (1) has a propeller-like structure because the molecularly twisted configuration hinders the fluorescence quenching of the molecules in the aggregated state, and is capable of emitting a strong fluorescence, that is, having aggregation-induced luminescence properties.
  • a -CN group with strong electron-withdrawing action and an aromatic amine group (Ar) with strong electron-acting action attached to tetraphenylbenzene The position of the para-phenyl ring (as shown in Figure 1, where D indicates the position at which the electron-withdrawing group Ar is bonded to tetraphenylbenzene, and A indicates the electron-withdrawing group - CN is linked to tetraphenylbenzene Position), strong electron absorption and strong push electron action and steric hindrance make the molecular emission spectrum red shift, can emit deep blue light of 450nm or less, and because of the intramolecular charge transfer, the molecule is also very strong in solution state. Fluorescence emission.
  • the aggregation-inducing blue light material in the embodiment of the invention also has good color purity and is an ideal choice for high color purity blue light materials.
  • the material Since the material has strong fluorescence emission in both the aggregated state and the dispersed state, it can be selected to be used directly for the luminescent layer luminescent material without doping, simplifying the process, and simultaneously undoping the aggregation-induced material film made of the blue material. Layer interface stability is good. It can be understood that the aggregation-inducing blue light material of the present invention can also be selected and used together with a suitable main blue light-emitting material, for example, the aggregation-inducing blue light material and the main blue light-emitting material are doped at a mass ratio of 1-10:100. Get higher luminous efficiency.
  • R 1 , R 2 , R 3 and R 4 are both H, and R 5 and R 6 are both -C(CH 3 ) 3 .
  • R 5 and R 6 in the structure of the compound are both -C(CH 3 ) 3 , that is, a carbazole group having a strong push electron action
  • the two benzene rings increase in the same -C (CH 3) 3 having electron donating effect, and -C (CH 3) 3 having a large steric hindrance, so that the degree of increased material molecules twisted configuration, thereby making the formula (1)
  • the aggregation of the structure induces the blue light material to emit more light in the aggregate state, and at the same time, the solubility of the material can be increased to facilitate the subsequent process of evaporation.
  • R 1 , R 2 , R 3 and R 4 are both H; and R 7 and R 8 are both -C(CH 3 ) 3 .
  • R 7 and R 8 in the structure of the compound are both -C(CH 3 ) 3 , that is, a diphenylamine group having a strong push electron action.
  • the two benzene rings add a t-butyl group which also has a push-electron effect, and -C(CH 3 ) 3 has a large steric hindrance, which makes the molecular structure of the material more distorted, plus because of the diphenylamine group.
  • the two phenyl groups in the group are free to rotate, which can further distort the molecular configuration of the entire material.
  • a second embodiment of the present invention provides a method for preparing an aggregation-inducing blue light material, and the method for preparing the aggregation-inducing blue light material includes step S100, step S200, and step S300.
  • the detailed steps are as follows.
  • Step S100 mixing 1,4-dibromo-2,5-diiodobenzene and benzene boron raw materials to produce a first reaction to obtain compound 1, and the benzene boron raw material is one or two of phenylboronic acid and phenylboronic acid ester.
  • the structure of the compound 1 is as shown in the formula (3):
  • the type of the first reaction is a Suzuki reaction, in which the molecular structure of the phenylborate is as shown in the formula (8): Formula (8).
  • Step S200 providing a triphenylamine-based raw material, wherein the triphenylamine-based raw material is a boronic acid group or a boronic acid ester group including a triphenylamine structure and a Suzuki reaction with the compound 1, and the triphenylamine-based raw material and the compound 1 are second.
  • the reaction gives the compound 2, and the structure of the compound 2 is as shown in the formula (5):
  • R 1 and R 2 are independently selected from the group consisting of H, —CH 3 and —C 2 H 6 ; and Ar is selected from the group consisting of aromatic amine groups represented by formula (2) and formula (3);
  • R 5 and R 6 are independently selected from the group consisting of H, —CH 3 and —C(CH 3 ) 3 ; and R 7 and R 8 are independently selected from H and —CH 3 , One of -C(CH 3 ) 3 .
  • the triphenylamine raw material includes a triphenylamine structure and a boric acid group or a borate ester group, wherein the triphenylamine structure provides a strong electron-donating group for the finally formed aggregation-inducing blue light material, and a boric acid group or a borate ester group is used. Suzuki reaction occurs with compound 1.
  • the structure of the triphenylamine-based raw material is one of the formulas (6) and (7);
  • R 1 and R 2 in the formula (6) and the formula (7) are each independently selected from one of H, -CH 3 and -C 2 H 6 , and Ar in the formula (6) and the formula (7) Each selected from the group consisting of aromatic amine groups represented by formula (2) and formula (3);
  • R 5 and R 6 are independently selected from the group consisting of H, -CH 3 and -C(CH 3 ) 3 ; in the formula (3), R 7 and R 8 are independently selected from H, One of -CH 3 and -C(CH 3 ) 3 .
  • Step S300 providing a cyanobenzene boron-based raw material, wherein the cyanobenzene boron-based raw material is one of substituted or unsubstituted 4-cyanobenzeneboronic acid and substituted or unsubstituted 4-cyanophenylboronic acid pinacol ester.
  • the cyanobenzone-based raw material undergoes a third reaction with the compound 2 to obtain an aggregation-inducing blue light material.
  • the aggregation-inducing blue light material is capable of emitting deep blue light having a wavelength of less than 450 nm, and has strong fluorescence emission in both the aggregated state and the dispersed state.
  • the third type of reaction is the Suzuki reaction.
  • R 3 and R 4 are independently selected from one of H, -CH 3 and -C 2 H 6 , it is understood that R 3 , R 4 and formula (1) herein in R 3, the same as R 4, i.e. the formula R (1) is 3, R 4 is derived from this.
  • R 3 and R 4 are independently selected from one of H, -CH 3 and -C 2 H 6 , it is also understood that R 3 , R 4 and formula (1) herein in R 3, the same as R 4, i.e. the formula R (1) is 3, R 4 is derived from this.
  • the aggregation-inducing blue light material prepared in the second embodiment has the same structure as the aggregation-inducing blue light material provided in the first embodiment.
  • a catalyst is added to the first, second, and third reactions, the catalyst comprising a palladium catalyst.
  • the palladium catalyst comprises tetrakis(triphenylphosphine)palladium. Tetrakis(triphenylphosphine)palladium catalyzes in the first reaction, the second reaction, and the third reaction.
  • the molar ratio of 1,4-dibromo-2,5-diiodobenzene, benzoboron starting material and palladium catalyst in the first reaction is 1,4-dibromo-2,5-diiodide.
  • Benzene: benzoboron starting material: palladium catalyst 1:2-3:0.02-0.1. A better yield can be obtained within this ratio range.
  • a good yield can be obtained in the range of the ratio, the yield of the final product is 80% or more, and the preferred yield is 87.3%.
  • the temperature of the first reaction is 65-80 ° C
  • the temperature of the second reaction is 65-80 ° C
  • the temperature of the third reaction is 100-120 ° C.
  • the first reaction, the second reaction, and the third reaction are both reacted in an oxygen free environment.
  • the catalytic activity of the palladium catalyst can be ensured in an anaerobic environment, especially to avoid the catalytic activity of tetrakis(triphenylphosphine)palladium being oxidized.
  • both the first reaction and the second reaction are carried out in a mixed solvent having an aqueous solution of tetrahydrofuran (THF) and potassium carbonate.
  • THF tetrahydrofuran
  • tetrahydrofuran (THF) has good solubility to the raw materials in the first reaction, the raw materials in the compound 1 and the second reaction, and the compound 2, and the potassium ions in the potassium carbonate can be activated.
  • the carbonate ion in the potassium carbonate can capture the iodide ion in the first reaction process or the first The bromide ion in the second reaction allows the first reaction or the second reaction to proceed efficiently.
  • the third reaction is carried out in a mixed solvent having an aqueous solution of toluene, ethanol and potassium carbonate.
  • a suitable reaction system environment for the third reaction the toluene and the ethanol have good solubility to the raw materials and the final product in the third reaction, and the potassium ions in the potassium carbonate can activate the cyanobenzene boron raw materials, in the potassium carbonate
  • the carbonate ion can capture the bromide ion in the third reaction process, so that the third reaction can be carried out efficiently.
  • the nuclear magnetic data of the target product 1 1H NMR (400 MHz, d-DMSO): ⁇ (TMS, ppm) 7.75 (d, 2H), 7.47 (d, 2H), 7.43 (d, 2H), 7.29 (m, 12H), 7.12 (d, 2H), 7.05 (t, 2H), 7.00 (t, 4H), 6.86 (d, 2H), 1.35 (s, 18H).
  • Compound 1 was prepared by the method of the first reaction in Example 1.
  • the target product 1, the target product 2 and the target product 3 in the above three examples were tested for performance, and the maximum fluorescence emission wavelength was mainly tested, and the data results are shown in Table 1.
  • Example product wavelength Example 1 Target product 1 448nm
  • the target product prepared by the three examples of the present invention has an emission wavelength of less than 450 nm, which is an ideal choice for the dark blue luminescent material.
  • the present invention also provides a display device 10 including a light-emitting layer 100 including an aggregation-inducing blue light material as in the above embodiment.
  • the aggregation-inducing blue light material has strong fluorescence emission in the light-emitting layer 100, and the molecule has a twisted configuration, which hinders fluorescence quenching in the aggregate state, and has strong fluorescence emission in both the aggregated state and the dispersed state. And capable of emitting deep blue light having a wavelength of less than 450 nm.
  • the use of the aggregation-inducing blue light material in the present invention can be selectively used as a light-emitting layer without doping, and the process is more simplified, and the interface stability of the material layer made of the undoped aggregation-inducing blue light material is better.
  • the aggregation-inducing blue light material is selected to be doped with other materials, due to the excellent characteristics of the aggregation-inducing blue light material of the present invention, higher luminous efficiency can be obtained after doping with other light-emitting materials in a suitable ratio, due to its aggregation state. It still has a strong fluorescence emission, so that the doping ratio which can be adjusted during doping is large, and it is not easy to be quenched by aggregation.
  • the luminescent layer 100 further includes a main blue luminescent material, and the mass ratio of the aggregation-inducing blue light material to the main blue luminescent material is 1-10:100. By performing doping with the mass ratio in this embodiment, higher luminous efficiency can be obtained.
  • the display device 10 further includes a substrate 200, a thin film transistor layer 300 disposed on the substrate 200, and the light emitting layer 100 is disposed on a side of the thin film transistor layer 300 away from the substrate 200.

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Abstract

本发明提供了一种聚集诱导蓝光材料，所述聚集诱导蓝光材料具有式(1)所示的分子结构：其中，所述式(1)中，R 1、R 2、R 3、R 4独立的选自H、-CH 3、-C 2H 6中的一种；Ar选自式(2)、式(3)所示的芳香胺基团；所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。本发明还提供一种聚集诱导蓝光材料的制备方法和显示装置。本发明提供的聚集诱导蓝光材料能够发出波长小于450nm的深蓝光，且在聚集状态具有很强的荧光发射。

Description

聚集诱导蓝光材料及其制备方法、显示装置 技术领域
本发明涉及显示技术领域，具体涉及一种聚集诱导蓝光材料及其制备方法、显示装置。
背景技术
有机发光二极管(Organic Light-Emitting Diode,OLED)显示器件具有自发光、广视角、高对比度、较低耗电、极高反应速度等优点。OLED器件中的发光材料通常在浓溶液或聚集态时会发生荧光猝灭的现象，为了使材料本身的效率在器件中得到最大的利用，一般要求材料的光谱峰位与目标峰位比较接近。目前，复合OLED器件中能发出光谱峰位与蓝光峰位相近且在聚集态下不易发生荧光猝灭的材料并不多。因此，开发该类有机蓝光材料是OLED显示技术急需攻克的难题。
发明内容
有鉴于此，本发明提供一种能发出深蓝光，且在聚集状态下具有很强的荧光发射的聚集诱导蓝光材料，具体技术方案如下所述。
一种聚集诱导蓝光材料，所述聚集诱导蓝光材料具有式(1)所示的分子结构：
Figure PCTCN2018087544-appb-000001
其中，所述式(1)中，R 1、R 2、R 3、R 4独立的选自H、-CH 3、-C 2H 6中 的一种；Ar选自式(2)、式(3)所示的芳香胺基团；
Figure PCTCN2018087544-appb-000002
所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
优选的，所述Ar为式(2)时，所述R 1、R 2、R 3、R 4均为H；所述R 5、R 6均为-C(CH 3) 3。
优选的，所述Ar为式(3)时，所述R 1、R 2、R 3、R 4均为H；所述R 7、R 8均为-C(CH 3) 3。
本发明还提供一种聚集诱导蓝光材料的制备方法，包括以下步骤：
将1,4-二溴-2,5-二碘苯和苯硼类原料混合发生第一反应得到化合物1，所述苯硼类原料为苯硼酸和苯硼酸酯中的一种或两种，所述化合物1结构如式(4)所示：
Figure PCTCN2018087544-appb-000003
提供三苯胺类原料，所述三苯胺类原料包括三苯胺结构和能与所述化合物1发生铃木反应的硼酸基团或者硼酸酯基团，将所述三苯胺类原料与所述化合物1混合发生第二反应得到化合物2，所述化合物2的结构如式(5)所示：
Figure PCTCN2018087544-appb-000004
其中所述R 1、R 2独立的选自H、-CH 3、-C 2H 6中的一种；Ar选自式(2)、式(3)所示的芳香胺基团；
Figure PCTCN2018087544-appb-000005
所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种；
提供氰基苯硼类原料，所述氰基苯硼类原料包括取代或未取代的4-氰基苯硼酸和取代或未取代的4-氰基苯硼酸频哪醇酯中的一种或多种，将所述氰基苯硼类原料与所述化合物2混合发生第三反应得到聚集诱导蓝光材料，其中所述聚集诱导蓝光材料具有式(1)所示的分子结构：
Figure PCTCN2018087544-appb-000006
其中，所述式(1)中，R 1、R 2、R 3、R 4独立的选自H、-CH 3、-C 2H 6中的一种；Ar选自式(2)、式(3)所示的芳香胺基团；
Figure PCTCN2018087544-appb-000007
所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
优选的，在所述第一反应、第二反应和第三反应中加入催化剂，所述催化剂包括钯催化剂。
优选的，所述钯催化剂包括四(三苯基膦)钯。
优选的，所述三苯胺类原料的结构为式(6)、式(7)所示中的一种：
Figure PCTCN2018087544-appb-000008
其中所述式(6)和式(7)中的R 1、R 2均独立的选自H、-CH 3、-C 2H 6中的一种，所述式(6)和式(7)中的Ar均选自式(2)、式(3)所示的芳香胺基团；
Figure PCTCN2018087544-appb-000009
所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；所述式(3)中，R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
优选的，所述第一反应中所述1,4-二溴-2,5-二碘苯、苯硼类原料和钯催化剂的用量摩尔比为1,4-二溴-2,5-二碘苯∶苯硼类原料∶钯催化剂＝1∶2-3∶0.02-0.1。
优选的，所述第二反应中所述化合物1、三苯胺类原料和钯催化剂的用量摩尔比为化合物1∶三苯胺类原料∶钯催化剂＝0.03-0.08∶0.03-0.08∶0.02-0.06。
优选的，所述第三反应中所述化合物2、氰基苯硼类原料和钯催化剂的用量摩尔比为化合物2∶氰基苯硼类原料∶钯催化剂＝0.1-0.5∶0.4-0.8∶0.01-0.03。
优选的，所述第一反应的温度为65-80℃，所述第二反应的温度为65-80℃，所述第三反应的温度为100-120℃。
优选的，所述第一反应、第二反应和所述第三反应均在无氧环境中发生。
本发明还提供一种显示装置，所述显示装置包括发光层，所述发光层中包 括如上述任一项所述的聚集诱导蓝光材料。
优选的，所述发光层中还包括主蓝光发光材料，所述聚集诱导蓝光材料与所述主蓝光发光材料的质量比为1-10∶100。
优选的，所述显示装置还包括基板、设置在所述基板上的薄膜晶体管层，所述发光层设置在所述薄膜晶体管层远离所述基板的一侧。
本发明的有益效果：本发明提供的聚集诱导蓝光材料能够发出波长小于450nm的深蓝光，且在聚集状态具有很强的荧光发射。
附图说明
为了更清楚地说明本发明实施例中的技术方案，下面将对实施例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性的前提下，还可以根据这些附图获得其他的附图。
图1为本发明第一实施例提供的聚集诱导蓝光材料中的推电子基团、拉电子基团与四苯基苯连接位置示意图。
图2为本发明第二实施例提供的一种聚集诱导蓝光材料的制备方法流程图。
图3为本发明提供的一种显示装置的结构示意图。
具体实施方式
下面将结合本发明实施例中的附图，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例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，本领域普通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，都属于本发明保护的范围。
本发明的说明书和权利要求书及所述附图中的术语“第一”、“第二”等是 用于区别不同对象，而不是用于描述特定顺序。此外，术语“包括”和“具有”以及它们任何变形，意图在于覆盖不排他的包含。例如包含了一系列步骤或单元的过程、方法、系统、产品或设备没有限定于已列出的步骤或单元，而是可选地还包括没有列出的步骤或单元，或可选地还包括对于这些过程、方法、产品或设备固有的其它步骤或单元。
在本文中提及“实施例”意味着，结合实施例描述的特定特征、结构或特性可以包含在本发明的至少一个实施例中。在说明书中的各个位置出现该短语并不一定均是指相同的实施例，也不是与其它实施例互斥的独立的或备选的实施例。本领域技术人员显式地和隐式地理解的是，本文所描述的实施例可以与其它实施例相结合。
本发明第一实施例提供一种聚集诱导蓝光材料，其具有式(1)所示的分子结构：
Figure PCTCN2018087544-appb-000010
其中，所述式(1)中，R 1、R 2、R 3、R 4独立的选自H、-CH 3、-C 2H 6中的一种；Ar选自式(2)、式(3)所示的芳香胺基团；
Figure PCTCN2018087544-appb-000011
所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
式(1)所示的分子结构具有螺旋桨状结构，因为分子扭曲的构型阻碍了 分子在聚集状态的荧光猝灭，能够发射很强的荧光，即具有聚集诱导发光性质。具有强吸电子作用的-CN基团和强推电子作用的芳香胺基团(Ar)接在四苯基苯
Figure PCTCN2018087544-appb-000012
的对位苯环的位置(如图1中所示，其中D指示的是推电子基团Ar与四苯基苯连接的位置，A指示的是拉电子基团-CN与四苯基苯连接的位置)，强吸电子和强推电子作用以及位阻作用使分子发射光谱红移，能够发射小于等于450nm的深蓝光，且因为分子内电荷转移作用，使得该分子在溶液状态下也有极强的荧光发射。四苯基苯的对位苯环上的基团(式1中的R 1、R 2、R 3和R 4)和芳香胺基团中的苯环上的基团(式2中的R 5和R 6，式3中的R 7和R 8)的空间位阻作用和电性诱导效应，使得材料分子构型更为扭曲，在聚集态发光更强，材料溶解性更好。本发明实施例中的聚集诱导蓝光材料还具有良好的色纯度，是高色纯度蓝光材料的理想选择。由于该材料在聚集态和分散状态下都有很强的荧光发射，可选择不进行掺杂直接用于发光层发光材料使用，简化工艺，同时不掺杂的聚集诱导蓝光材料制成的材料膜层界面稳定性好。可以理解的是，本发明的聚集诱导蓝光材料还可选择和合适的主蓝光发光材料搭配使用，例如将聚集诱导蓝光材料与主蓝光发光材料按照质量比为1-10:100进行掺杂，可以获得更高的发光效率。
在进一步的实施例中，Ar为式(2)时，R 1、R 2、R 3、R 4均为H，R 5、R 6均为-C(CH 3) 3。该化合物结构中的R 5和R 6均为-C(CH 3) 3，即在具有强推电子作用的咔唑基团
Figure PCTCN2018087544-appb-000013
的两个苯环上增加同样具有推电子作用的-C(CH 3) 3，且-C(CH 3) 3具有较大的空间位阻，使得材料分子构型扭曲程度加大，进而使得式(1)结构的聚集诱导蓝光材料在聚集态时发光更强，同时可以增加材料的 溶解性，以利于蒸镀完成后续制程。
在进一步的实施例中，Ar为式(3)时，R 1、R 2、R 3、R 4均为H；R 7、R 8均为-C(CH 3) 3。该化合物结构中的R 7、R 8均为-C(CH 3) 3，即在具有强推电子作用的二苯胺基团
Figure PCTCN2018087544-appb-000014
的两个苯环上增加同样具有推电子作用的叔丁基，且-C(CH 3) 3具有较大的空间位阻，使得材料分子构型扭曲程度加大，再加上因为二苯胺基团中的两个苯基能够自由旋转，能够促使整个材料分子构型进一步扭曲。上述原因使得该实施例中的聚集诱导蓝光材料在聚集态时发光更强，同时可以增加材料的溶解性，以利于蒸镀完成后续制程。
请参阅图2，本发明第二实施例提供一种聚集诱导蓝光材料的制备方法，所述聚集诱导蓝光材料的制备方法包括步骤S100、步骤S200和步骤S300。详细步骤如下所述。
步骤S100，将1,4-二溴-2,5-二碘苯和苯硼类原料混合发生第一反应得到化合物1,苯硼类原料为苯硼酸和苯硼酸酯中的一种或两种，所述化合物1结构如式(3)所示：
Figure PCTCN2018087544-appb-000015
式(3)。第一反应的类型为铃木反应，其中苯硼酸酯的分子结构如式(8)所示：
Figure PCTCN2018087544-appb-000016
式(8)。
步骤S200，提供三苯胺类原料，三苯胺类原料为包括三苯胺结构和能与所述化合物1发生铃木反应的硼酸基团或者硼酸酯基团，将三苯胺类原料与化合物1发生第二反应得到化合物2，所述化合物2的结构如式(5)所示：
Figure PCTCN2018087544-appb-000017
其中所述R 1、R 2独立的选自H、-CH 3、-C 2H 6中的一种；Ar选自式(2)、式(3)所示的芳香胺基团；
Figure PCTCN2018087544-appb-000018
所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
三苯胺类原料中包括三苯胺结构和硼酸基团或者硼酸酯基团，其中三苯胺结构为最终形成的聚集诱导蓝光材料提供强推电子基团，硼酸基团或者硼酸酯基团用于与化合物1发生铃木反应。
在进一步的实施例中，三苯胺类原料的结构为式(6)、式(7)所示中的一种；
Figure PCTCN2018087544-appb-000019
其中式(6)和式(7)中的R 1、R 2均独立的选自H、-CH 3、-C 2H 6中的一种，式(6)和式(7)中的Ar均选自式(2)、式(3)所示的芳香胺基团；
Figure PCTCN2018087544-appb-000020
式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；式(3)中，R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
步骤S300，提供氰基苯硼类原料，所述氰基苯硼类原料为取代或未取代的4-氰基苯硼酸和取代或未取代的4-氰基苯硼酸频哪醇酯中的一种或两种，所述氰基苯硼类原料与化合物2发生第三反应得到聚集诱导蓝光材料。聚集诱导蓝光材料能够发出波长小于450nm的深蓝光，且在聚集状态和分散状态下都有很强的荧光发射。第三反应的类型为铃木反应。其中取代或未取代的4-氰基苯硼酸的结构如式(9)所示：
Figure PCTCN2018087544-appb-000021
式(9)，其中R 3、R 4独立的选自H、-CH 3、-C 2H 6中的一种，可以理解的是，此处的R 3、R 4与式(1)中的R 3、R 4相同，即式(1)中的R 3、R 4来源于此。取代或未取代的4-氰基苯硼酸频哪醇酯的结构如式(10)所示：
Figure PCTCN2018087544-appb-000022
式(10)，其中R 3、R 4独立的选自H、-CH 3、-C 2H 6中的一种，同样可以理解的是，此处的R 3、R 4与式(1)中的R 3、R 4相同，即式(1)中的R 3、R 4来源于此。
其中第二实施例中制备得到的聚集诱导蓝光材料与第一实施例提供的聚集诱导蓝光材料的结构相同。
进一步的实施例中，在第一反应、第二反应和第三反应中加入催化剂，所述催化剂包括钯催化剂。优选的，所述钯催化剂包括四(三苯基膦)钯。四(三苯基膦)钯在第一反应、第二反应和第三反应起催化作用。
进一步的实施例中，第一反应中1,4-二溴-2,5-二碘苯、苯硼类原料和钯催化剂的用量摩尔比为1,4-二溴-2,5-二碘苯∶苯硼类原料∶钯催化剂＝1∶2-3∶0.02-0.1。在该比例范围内能够得到较好的产率。
进一步的实施例中，第二反应中化合物1、三苯胺类原料和钯催化剂的用量摩尔比为化合物1∶三苯胺类原料∶钯催化剂＝0.03-0.08∶0.03-0.08∶ 0.02-0.06。在该比例范围内能够得到较好的产率。
进一步的实施例中，所述第三反应中所述化合物2、氰基苯硼类原料和钯催化剂的用量摩尔比为化合物2∶氰基苯硼类原料∶钯催化剂＝0.1-0.5∶0.4-0.8∶0.01-0.03。在该比例范围内能够得到较好的产率，最终产物的产率为80％以上，较优产率达到87.3％。
进一步的实施例中，第一反应的温度为65-80℃，第二反应的温度为65-80℃，第三反应的温度为100-120℃。在上述温度范围内发生反应，能够使每一个反应顺利进行，同时能够使反应原料反应更完全。
进一步的实施例中，第一反应、第二反应和第三反应均在无氧环境中反应。在无氧环境下可以保证钯催化剂的催化活性，尤其是避免四(三苯基膦)钯被氧化而失去催化活性。
进一步的实施例中，第一反应和第二反应均在具有四氢呋喃(THF)和碳酸钾水溶液的混合溶剂中反应。为第一反应提供合适的反应体系环境，四氢呋喃(THF)对第一反应中的原料、化合物1和第二反应中的原料、化合物2具有较好的溶解性，碳酸钾中的钾离子能够活化第一反应过程中苯硼类原料或者第二反应过程中三苯胺类原料中的硼酸基团或者硼酸酯基团，碳酸钾中的碳酸根离子能够夺取第一反应过程中的碘离子或者第二反应中的溴离子，使第一反应或者第二反应有效进行。
进一步的实施例中，第三反应在具有甲苯、乙醇和碳酸钾水溶液的混合溶剂中反应。为第三反应提供合适的反应体系环境，甲苯、乙醇对第三反应中的原料、最终产物具有较好的溶解性，碳酸钾中的钾离子能够活化氰基苯硼类原料，碳酸钾中的碳酸根离子能够夺取第三反应过程中的溴离子，使第三反应有效进行。
下面将通过具体实施例对本发明作进一步的阐述，但本发明并不限于此特 定例子。
实施例1
第一反应，将1,4-二溴-2,5-二碘苯(974.5mg,2mmol)，苯硼酸(609.5mg,5mmol),四(三苯基膦)钯(115.6mg 0.1mmol)加入到三口烧瓶中，再往三口烧瓶中加入20mL THF和碳酸钾水溶液(10mL,2M)，通入氮气，在74℃下回流反应8h后，结束反应，将产物分离提纯，得到化合物1。化合物1的结构式如式(3)所示。
第二反应，将1,1-二叔丁基-4-溴苯硼酸三苯胺(243mg,0.5mmol)，化合物1(19.4mg,0.5mmol)及四(三苯基膦)钯(46.2mg,0.04mmol)加入到洁净的三口烧瓶中，再往该三口烧瓶中加入20mL THF和碳酸钾水溶液(10mL,2M)，通入氮气，在74℃下回流反应5h后，分离提纯得到化合物2a。化合物2a的结构式如式(11)所示：
Figure PCTCN2018087544-appb-000023
式(11)。
第三反应，将化合物2a(198.9mg,0.3mmol)，4-氰基苯硼酸(88.2mg，0.6mmol)，四(三苯基膦)钯(17.3mg,0.015mmol)加入到洁净的三口烧瓶中，再往该三口烧瓶中加入甲苯10mL、无水乙醇5mL和碳酸钾的水溶液(5mL,2M)，通入氮气，在110℃下回流反应8h后，分离提纯得到目标产物1，目标产物1的质量为180.4mg，计算产率为87.3％。目标产物1的结构式如式(12)所示：
Figure PCTCN2018087544-appb-000024
式(12)。其中，目标产物1的核磁数据：1H NMR(400MHz,d-DMSO):δ(TMS,ppm)7.75(d,2H),7.47(d,2H),7.43(d,2H),7.29(m,12H),7.12(d,2H),7.05(t,2H),7.00(t,4H),6.86(d,2H),1.35(s,18H)。
制备流程图如下式(13)所示。
式(13)，
Figure PCTCN2018087544-appb-000025
实施例2
第一反应，将1,4-二溴-2,5-二碘苯(974.5mg,2mmol)，苯硼酸(609.5mg,5mmol),四(三苯基膦)钯(115.6mg 0.1mmol)加入到三口烧瓶中，再往三口烧瓶中加入20mL THF和碳酸钾水溶液(10mL,2M)，通入氮气，在74℃下回流反应8h后，反应结束提纯，得到化合物1。化合物1的结构式如式(3)所示。
第二反应，将结构式如式(14)所示的三苯胺原料(241mg,0.5mmol)，
Figure PCTCN2018087544-appb-000026
式(14)，化合物1(19.4mg,0.5mmol)及四(三苯基膦)钯(46.2mg,0.04mmol)加入到洁净的三口烧瓶中，再往该三口烧瓶中加入20mL THF和碳酸钾水溶液(10mL,2M)，通入氮气，在74℃下回流反应5h后，分离提纯得到化合物2b。化合物2b的结构式如式(15)所示：
Figure PCTCN2018087544-appb-000027
式(15)。
第三反应，将化合物2b(198.6mg,0.3mmol)，(4-氰基-2,6-二甲基)苯硼酸(105mg，0.6mmol)，四(三苯基膦)钯(17.3mg,0.015mmol)加入到洁净的三口烧瓶中，再往该三口烧瓶中加入甲苯10mL、无水乙醇5mL和碳酸钾的水溶液(5mL,2M)，通入氮气，在110℃下回流反应8h后，分离提纯得到目标产物2，目标产物2的质量为190.4mg，计算产率为88.9％。目标产物2的结构式如式(16)所示：
Figure PCTCN2018087544-appb-000028
式(16)。制备流程图如下式(17)所示。
式(17)，
Figure PCTCN2018087544-appb-000029
实施例3
参考实施例1中第一反应的方法制备得到化合物1。
第二反应，将结构式如式(18)的三苯胺原料(145mg,0.5mmol)，
Figure PCTCN2018087544-appb-000030
式(18)，化合物1(19.4mg,0.5mmol)及四(三苯基膦)钯(46.2mg,0.04mmol)加入到洁净的三口烧瓶中，再往该三口烧瓶中加入20mL THF 和碳酸钾水溶液(10mL,2M)，通入氮气，在74℃下回流反应5h后，分离提纯得到化合物2c。化合物2c的结构式如式(19)所示：
Figure PCTCN2018087544-appb-000031
式(19)。
将化合物2c(165.3mg,0.3mmol)，4-氰基苯硼酸(88.2mg，0.6mmol)，四(三苯基膦)钯(17.3mg,0.015mmol)加入到洁净的三口烧瓶中，再往该三口烧瓶中加入甲苯10mL、无水乙醇5mL和碳酸钾的水溶液(5mL,2M)，通入氮气，在110℃下回流反应8h后，分离提纯得到目标产物2，目标产物2的质量为148.2mg，计算产率为86.2％。目标产物3的结构式如式(20)所示：
Figure PCTCN2018087544-appb-000032
式(20)。制备流程图如下式(21)所示。
式(21)，
Figure PCTCN2018087544-appb-000033
效果实施例
将上述三个实施例中的目标产物1、目标产物2和目标产物3进行性能测试，主要测试最大荧光发射波长，得出数据结果如表1所示。
表1
实施例 产物 波长
实施例1 目标产物1 448nm
实施例2 目标产物2 442nm
实施例3 目标产物3 436nm
从上述表1中的测试结果可以看出，本发明三个实施例制备得到的目标产物的发光波长小于450nm，是深蓝发光材料的理想选择。
请参阅图3，本发明还提供一种显示装置10，所述显示装置10包括发光层100，所述发光层100中包括如上述实施例中的聚集诱导蓝光材料。该聚集诱导蓝光材料在发光层100中具有很强的荧光发射，分子具有扭曲的构型，阻碍了其在聚集态时的荧光猝灭，在聚集态和分散状态下都有很强的荧光发射，且能够发射波长小于450nm的深蓝光。采用本发明中的聚集诱导蓝光材料可以选择不进行掺杂直接做成发光层使用，工艺更简化，同时采用不掺杂的聚集诱导蓝光材料制成的材料膜层界面稳定性更好。当选择将该聚集诱导蓝光材料与其他材料进行掺杂时，由于本发明聚集诱导蓝光材料的优异特性，与合适比例的其他发光材料掺杂后能获得更高的发光效率，由于其在聚集态时仍具有很强的荧光发射，使得掺杂时可调整的掺杂比例范围较大，且不易因聚集而淬灭。
在进一步的实施例中，所述发光层100中还包括主蓝光发光材料，所述聚集诱导蓝光材料与所述主蓝光发光材料的质量比为1-10∶100。采用该实施例中质量比进行掺杂，可以获得更高的发光效率。
在进一步的实施例中，所述显示装置10还包括基板200、设置在所述基板200上的薄膜晶体管层300，所述发光层100设置在薄膜晶体管层300远离基板200的一侧。
以上所述实施例仅表达了本发明的几种实施方式，其描述较为具体和详细，但并不能因此而理解为对本发明专利范围的限制。应当指出的是，对于本 领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干变形和改进，这些都属于本发明的保护范围。因此，本发明专利的保护范围应以所附权利要求为准。

Claims (15)

  1. 一种聚集诱导蓝光材料，其特征在于，所述聚集诱导蓝光材料具有式(1)所示的分子结构：
    Figure PCTCN2018087544-appb-100001
    其中，所述式(1)中，R 1、R 2、R 3、R 4独立的选自H、-CH 3、-C 2H 6中的一种；Ar选自式(2)、式(3)所示的芳香胺基团；
    Figure PCTCN2018087544-appb-100002
    所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
  2. 如权利要求1所述的聚集诱导蓝光材料，其特征在于，所述Ar为式(2)时，所述R 1、R 2、R 3、R 4均为H；所述R 5、R 6均为-C(CH 3) 3。
  3. 如权利要求1所述的聚集诱导蓝光材料，其特征在于，所述Ar为式(3)时，所述R 1、R 2、R 3、R 4均为H；所述R 7、R 8均为-C(CH 3) 3。
  4. 一种聚集诱导蓝光材料的制备方法，其特征在于，包括以下步骤：
    将1,4-二溴-2,5-二碘苯和苯硼类原料混合发生第一反应得到化合物1，所述苯硼类原料为苯硼酸和苯硼酸酯中的一种或两种，所述化合物1结构如式 (4)所示：
    Figure PCTCN2018087544-appb-100003
    提供三苯胺类原料，所述三苯胺类原料包括三苯胺结构和能与所述化合物1发生铃木反应的硼酸基团或者硼酸酯基团，将所述三苯胺类原料与所述化合物1混合发生第二反应得到化合物2，所述化合物2的结构如式(5)所示：
    Figure PCTCN2018087544-appb-100004
    其中所述R 1、R 2独立的选自H、-CH 3、-C 2H 6中的一种；Ar选自式(2)、式(3)所示的芳香胺基团；
    Figure PCTCN2018087544-appb-100005
    所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种；
    提供氰基苯硼类原料，所述氰基苯硼类原料包括取代或未取代的4-氰基苯硼酸和取代或未取代的4-氰基苯硼酸频哪醇酯中的一种或多种，将所述氰基苯硼类原料与所述化合物2混合发生第三反应得到聚集诱导蓝光材料，其中所述聚集诱导蓝光材料具有式(1)所示的分子结构：
    Figure PCTCN2018087544-appb-100006
    其中，所述式(1)中，R 1、R 2、R 3、R 4独立的选自H、-CH 3、-C 2H 6中 的一种；Ar选自式(2)、式(3)所示的芳香胺基团；
    Figure PCTCN2018087544-appb-100007
    所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
  5. 如权利要求4所述的聚集诱导蓝光材料的制备方法，其特征在于，在所述第一反应、第二反应和第三反应中加入催化剂，所述催化剂包括钯催化剂。
  6. 如权利要求5所述的聚集诱导蓝光材料的制备方法，其特征在于，所述钯催化剂包括四(三苯基膦)钯。
  7. 如权利要求4所述的聚集诱导蓝光材料的制备方法，其特征在于，所述三苯胺类原料的结构为式(6)、式(7)所示中的一种：
    Figure PCTCN2018087544-appb-100008
    其中所述式(6)和式(7)中的R 1、R 2均独立的选自H、-CH 3、-C 2H 6中的一种，所述式(6)和式(7)中的Ar均选自式(2)、式(3)所示的芳香胺基团；
    Figure PCTCN2018087544-appb-100009
    所述式(2)中，R 5、R 6独立的选自H、-CH 3、-C(CH 3) 3中的一种；所述式(3)中，R 7、R 8独立的选自H、-CH 3、-C(CH 3) 3中的一种。
  8. 如权利要求5所述的聚集诱导蓝光材料的制备方法，其特征在于，所述第一反应中所述1,4-二溴-2,5-二碘苯、苯硼类原料和钯催化剂的用量摩尔比为1,4-二溴-2,5-二碘苯∶苯硼类原料∶钯催化剂＝1∶2-3∶0.02-0.1。
  9. 如权利要求5所述的聚集诱导蓝光材料的制备方法，其特征在于，所述第二反应中所述化合物1、三苯胺类原料和钯催化剂的用量摩尔比为化合物1∶三苯胺类原料∶钯催化剂＝0.03-0.08∶0.03-0.08∶0.02-0.06。
  10. 如权利要求5所述的聚集诱导蓝光材料的制备方法，其特征在于，所述第三反应中所述化合物2、氰基苯硼类原料和钯催化剂的用量摩尔比为化合物2∶氰基苯硼类原料∶钯催化剂＝0.1-0.5∶0.4-0.8∶0.01-0.03。
  11. 如权利要求4所述的聚集诱导蓝光材料的制备方法，其特征在于，所述第一反应的温度为65-80℃，所述第二反应的温度为65-80℃，所述第三反应的温度为100-120℃。
  12. 如权利要求4所述的聚集诱导蓝光材料的制备方法，其特征在于，所述第一反应、第二反应和所述第三反应均在无氧环境中发生。
  13. 一种显示装置，其特征在于，所述显示装置包括发光层，所述发光层中包括如权利要求1-3任一项所述的聚集诱导蓝光材料。
  14. 如权利要求13所述的显示装置，其特征在于，所述发光层中还包括主蓝光发光材料，所述聚集诱导蓝光材料与所述主蓝光发光材料的质量比为1-10∶100。
  15. 如权利要求13所述的显示装置，其特征在于，所述显示装置还包括基板、设置在所述基板上的薄膜晶体管层，所述发光层设置在所述薄膜晶体管层远离所述基板的一侧。
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