Condensed-ring compound and preparation method and application thereof

A compound and fused ring technology, applied in the field of fused ring compounds and their preparation, can solve the problems of reduced luminous efficiency, shortened service life, and low energy transfer efficiency of devices

Inactive Publication Date: 2020-01-17
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, the technical problem to be solved by the present invention is to overcome the defects of low stability and low energy transfer efficiency of the main material of the light-emit

Method used

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  • Condensed-ring compound and preparation method and application thereof
  • Condensed-ring compound and preparation method and application thereof
  • Condensed-ring compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] This embodiment provides a kind of condensed ring compound (compound 1), has the structure shown in the following formula:

[0084]

[0085] The synthetic route of compound 1 is as follows:

[0086]

[0087] Wherein, the synthetic route of intermediate 5-E is as follows:

[0088]

[0089] The preparation method of compound 1 specifically comprises the following steps:

[0090] (1) Synthesis of intermediate 1-E:

[0091]Get 500 milliliters of double-necked round-bottomed flasks and put into stirrer bar and connect reflux tube, fill with nitrogen after drying; Add compound o-nitrophenylboronic acid (16.70 grams, 1 equivalent), o-bromoiodobenzene (28.19 grams, 1.0 equivalent), potassium carbonate (K 2 CO 3 , 1.5 equivalents), ethanol (50 ml), water (50 ml), toluene (200 ml), tetrakis(triphenylphosphine) palladium (Pd(PPh 3 ) 4 , 0.05 equivalent), then heated to reflux and reacted for 12 hours, cooled to room temperature after the reaction was completed; adde...

Embodiment 2

[0104] This embodiment provides a kind of condensed ring compound (compound 2), has the structure shown in the following formula:

[0105]

[0106] The synthetic route of compound 2 is as follows:

[0107]

[0108] Wherein, the synthetic route of intermediate 5-E' is as follows:

[0109]

[0110] The preparation method of compound 2 specifically comprises the following steps:

[0111] (1) Synthesis of intermediate 1-E':

[0112] The same as the synthetic method of intermediate 1-E, the difference is that 1-bromo-8 iodonaphthalene (31.89 grams, 1 equivalent) is used to replace o-bromoiodobenzene, and the ratio of each raw material is adjusted to obtain intermediate 1-E' (22.56 grams, producing rate 69%)

[0113] (2) Synthesis of intermediate 2-E':

[0114] The same as the synthetic method of intermediate 2-E, the difference is that intermediate 1-E' (32.70 g, 1 equivalent) is used to replace intermediate 1-E, and the ratio of each raw material is adjusted to obtain...

Embodiment 3

[0125] This embodiment provides a condensed ring compound (compound 3), which has the structure shown in the following formula:

[0126]

[0127] The synthetic route of compound 3 is as follows:

[0128]

[0129] Wherein, the synthetic route of intermediate 5-E is the same as that of Example 1.

[0130] The preparation method of compound 3 specifically comprises the following steps:

[0131] (1)-(5) are the same as embodiment 1;

[0132] (6) Synthesis of compound 3:

[0133] The same synthesis method as compound 1, except that compound 1-2 (22.40 g, 1 equivalent) was used instead of compound 1-1, and the ratio of each raw material was adjusted to obtain compound 3 (35.24 g, yield 81%).

[0134] Elemental Analysis: C 30 h 17 N 30 Theoretical: C, 82.74; H, 3.93; N, 9.65; Found: C, 82.75; H, 3.95; N, 9.62; + ): theoretical value: 435.1372; measured value: 435.1377.

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Abstract

The invention discloses a condensed-ring compound and a preparation method and an application thereof. The condensed-ring compound has a structure represented by formula (I) or formula (II). The HOMOand LUMO energy levels of the fused-ring compound are completely separated, so that the energy gap width of the material is reduced, the three-wire energy level is improved, and the energy backflow from the object material to the main material is avoided to reduce the luminous efficiency; HOMO and LUMO energy levels are matched with adjacent materials, and the driving voltage is small. The devicehas large molecular structure size and good intramolecular conjugation, so it has good thermal stability, can avoid thermal decomposition of materials during film formation or use, avoids loss of material layer function, and improves luminous efficiency and luminous performance of the device. The invention also provides a preparation method of the fused-ring compound and its application as an organic electroluminescent material.

Description

technical field [0001] The invention relates to the field of display technology, in particular to a condensed ring compound and its preparation method and application. Background technique [0002] In 1987, Dr. Deng Qingyun and others from the laboratory of Eastman Kodak in the United States made the first organic light-emitting diode (OLED) device by vacuum evaporation for the first time, which is transparent and conductive. Indium tin oxide (ITO) is used as the anode, and diamine derivatives and tris(8-hydroxyquinoline)aluminum are sequentially evaporated on it, and magnesium-silver alloy is used as the cathode material. This multilayer structure can reduce the OLED device The driving voltage is high, and the problem of charge injection between the material molecule and the electrode interface is effectively improved, and the device performance and life are also improved. [0003] Compared with inorganic electroluminescent devices (electro luminescence devices, ELDs), OLE...

Claims

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Application Information

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IPC IPC(8): C07D209/94C07D401/14C07D403/04C07D403/10C07D409/04C07D413/04C07D487/04C07D491/048C07D495/04C07F9/6568C09K11/06H01L51/54
CPCC07D403/10C07D413/04C07D401/14C07F9/65685C07D409/04C07D209/94C07D403/04C07D491/048C07D495/04C07D487/04C09K11/06C09K2211/1059C09K2211/1029C09K2211/1048C09K2211/1096C09K2211/1092C09K2211/1044C09K2211/1033C09K2211/1037H10K85/654H10K85/6565H10K85/657H10K85/6572
Inventor 李祥智蔡烨魏定纬陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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