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Compound with dibenzo six-membered ring as core, and preparation method and application of compound

A technology of dibenzo six-membered rings and compounds, which is applied in the fields of compounds of Group 4/14 elements of the periodic table, organic silicon compounds, chemical instruments and methods, etc., can solve problems such as different performances

Active Publication Date: 2020-11-17
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Compound with dibenzo six-membered ring as core, and preparation method and application of compound
  • Compound with dibenzo six-membered ring as core, and preparation method and application of compound
  • Compound with dibenzo six-membered ring as core, and preparation method and application of compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0079] Intermediate D was synthesized according to the preparation method of intermediate D-1, and the specific structure is shown in Table 1.

[0080] Table 1

[0081]

[0082]

[0083]

[0084]

Embodiment 1

[0085] Embodiment 1: preparation compound 15

[0086]

[0087] Under nitrogen atmosphere, add 0.01mol intermediate D-1, 0.015mol raw material 4-1, 0.03mol sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 and 5×10 -5 mol of tri-tert-butylphosphine, then add 150ml of toluene to dissolve it, heat to 100°C, reflux for 24 hours, observe the reaction by TLC until the reaction is complete. Naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated until there was no fraction. The obtained substance was purified by silica gel column (petroleum ether as eluent) to obtain the target product with a purity of 99.41% and a yield of 67.2%.

[0088] Elemental analysis structure (molecular formula C 61 h 42 N 2 O): Theoretical: C, 89.46; H, 5.17; N, 3.42; O, 1.95; Tested: C, 89.47; H, 5.15; N, 3.40; ESI-MS(m / z)(M + ): The theoretical value is 818.33, and the measured value is 818.57. Proton NMR analysis: 8.01(dd,1H),7.61–7.52(m,9H),7.48(td,1H),7.44–7.3...

Embodiment 2

[0089] Embodiment 2: preparation compound 20

[0090]

[0091] Prepared according to the synthesis method of compound 1, except that intermediate D-2 is used instead of intermediate D-1, the purity of the obtained target product is 99.81%, and the yield is 79.3%.

[0092] Elemental analysis structure (molecular formula C 67 h 46 N 2 O): Theoretical: C, 89.90; H, 5.18; N, 3.13; O, 1.79; Tested: C, 89.92; H, 5.19; N, 3.12; ESI-MS(m / z)(M + ): The theoretical value is 894.36, and the measured value is 894.24. NMR analysis: 8.01(dd,1H),7.60(dt,2H),7.60–7.54(m,5H),7.57–7.51(m,3H),7.48(td,1H),7.42–7.31(m, 10H), 7.32(s,1H), 7.31–7.16(m,11H), 7.14(dd,4H), 7.15–7.06(m,6H), 7.02(ddd,2H).

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Abstract

The invention discloses a compound with a dibenzo six-membered ring as a core, and a preparation method belonging to the technical field of semiconductors. The structure of the compound provided by the invention is as shown in a general formula (1) which is described in the specification. The compound provided by the invention contains a dibenzo six-membered ring structure has very strong rigidity; and after connection with a five-membered ring fused ring or a six-membered ring fused ring or a seven-membered ring fused ring, the compound has the characteristics of difficulty in crystallizationand aggregation among molecules and good film-forming property; According to the compound disclosed by the invention, due to different electron donating capacities of a branched chain structure, HOMOenergy levels of the compound are different, and the compound can be used as a material for different functional layers; in addition, the compound provided by the invention has a relatively high triplet state energy level, can effectively block energy loss, and is beneficial for energy transfe; and therefore, after the compound provided by the invention is applied to an OLED device as an organicelectroluminescent functional layer material, the efficiency of the device is greatly improved, and the service life of the device is greatly prolonged.

Description

technical field [0001] The invention relates to a compound with a dibenzo six-membered ring as the core, a preparation method and an application thereof, belonging to the technical field of semiconductors. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positive and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D471/04C07D471/10C07D498/04C07D405/14C07D405/12C07D491/052C07D491/056C07D221/18C07D413/12C07D498/20C07D495/04C07D241/38C07D487/04C07D403/12C07D497/04C07D513/04C07D495/22C07D491/107C07D401/14C07D223/32C07F7/08C07D405/04C07D403/04C09K11/06H01L51/50H01L51/54
CPCC07D491/048C07D471/04C07D471/10C07D498/04C07D405/14C07D405/12C07D491/052C07D491/056C07D221/18C07D413/12C07D498/20C07D495/04C07D241/38C07D487/04C07D403/12C07D497/04C07D513/04C07D495/22C07D491/107C07D401/14C07D223/32C07F7/0812C07F7/0816C07D405/04C07D403/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096H10K85/615H10K85/631H10K85/636H10K85/626H10K85/633H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K85/40H10K50/18H10K50/15Y02E10/549
Inventor 张宇阳李崇张兆超吴秀芹
Owner JIANGSU SUNERA TECH CO LTD
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