Compound, organic light emitting display panel and display device

A light-emitting display and compound technology, applied in silicon organic compounds, organic chemistry, light-emitting materials, etc., can solve the problems of poor stability of phosphorescent devices and roll-off of phosphorescent material efficiency, and achieve the suppression of non-radiative transition process and high-efficiency energy transfer , the effect of wide optical bandgap

CN109956965BActive Publication Date: 2021-12-17WUHAN TIANMA MICRO ELECTRONICS CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Publication Date
2021-12-17

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Abstract

The invention belongs to the field of OLED technology and provides a compound with a D-σ-A chemical structure, the compound has a structure shown in Chemical Formula 1; wherein, D is an electron-donating group, and m is selected from 1, 2, and 3; A is an electron-accepting group, n is selected from 1, 2, and 3; D is mainly selected from substituted or unsubstituted C12-C40 carbazole groups, substituted or unsubstituted C13-C40 acridinium groups, A substituted or unsubstituted C12‑C40 diphenylamine group; A is selected from any one of aryl boron substituents, benzophenone substituents, aromatic heterocyclic ketone substituents, and sulfone substituents . The invention forms a non-conjugated connection by connecting an electron-donating group and an electron-accepting group on the tetraphenyl silicon core, and has a D-σ-A molecular structure. In particular, the introduction of the electron-accepting group A can make the entire compound molecule bipolar, which is beneficial to the transport of electrons and holes.
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Description

technical field

[0001] The present invention relates to the technical field of organic electroluminescence materials, in particular to a compound having a D-σ-A chemical structure and an organic light-emitting display panel and a display device comprising the compound. Background technique

[0002] With the development of electronic display technology, organic light-emitting devices (OLEDs) are widely used in various display devices, and the research and application of OLED light-emitting materials are also increasing.

[0003] According to the light-emitting mechanism, the materials used for OLED light-emitting layer mainly include:

[0004] (1) fluorescent material; (2) phosphorescent material.

[0005] For fluorescent materials, according to spin statistics, the ratio of singlet and triplet excitons in excitons is 1:3, so the maximum internal quantum yield of fluorescent materials does not exceed 25%. According to the Lambertian light emission mode, the light extraction...

Examples

Embodiment 1

[0085] Synthesis of Compound P1

[0086]

[0087] Weigh S1 (4.00mmol), S2 (2.00mmol), CuI (0.20mmol), trans-1,2-diaminocyclohexane (0.4mmol), anhydrous K 3 PO 4 (4.20 mmol), under a nitrogen atmosphere, 16 mL of toluene was added, and reacted at 110° C. for 24 h. The reaction mixture was cooled to room temperature. An appropriate amount of aqueous ammonium chloride solution was added to quench the reaction mixture. Extract the organic phase with dichloromethane (50mL) 3 times, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography using n-hexane / dichloromethane (3 / 1) as eluent, and finally purified to give solid S3 (1.2 mmol, 60%).

[0088] MALDI-TOF MS: m / z calculated: C 36 h 26 BrNSi: 579.1; Measured: 579.4

[0089]

[0090] Under the condition of nitrogen protec...

Embodiment 2

[0103] Synthesis of Compound P8

[0104]

[0105] Weigh S1 (8.0mmol), S8 (4.0mmol), CuI (0.4mmol), trans 1,2-diaminocyclohexane (0.48mmol), anhydrous K 3 PO 4 (8.0 mmol), under a nitrogen atmosphere, 40 mL of toluene was added, and reacted at 110° C. for 24 h. The reaction mixture was cooled to room temperature. An appropriate amount of aqueous ammonium chloride solution was added to quench the reaction mixture. Extract the organic phase with dichloromethane (80mL) 3 times, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography using n-hexane / dichloromethane (3 / 1) as eluent, and finally purified to give solid S9 (2.4 mmol, 60%).

[0106] MALDI-TOF MS: m / z calculated: C 39 h 32 BrNSi(S9): 621.2; Measured: 621.3.

[0107]

[0108] In a 100ml three-necked flask, first...

Embodiment 3

[0114] Synthesis of Compound P14

[0115]

[0116] Weigh S1 (6.0mmol), S12 (3.0mmol), CuI (0.3mmol), trans-1,2-diaminocyclohexane (0.35mmol), anhydrous K 3 PO 4 (6.0 mmol), under a nitrogen atmosphere, 40 mL of toluene was added, and reacted at 110° C. for 24 h. The reaction mixture was cooled to room temperature. An appropriate amount of aqueous ammonium chloride solution was added to quench the reaction mixture. Extract the organic phase with dichloromethane (80mL) 3 times, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography using n-hexane / dichloromethane (3 / 1) as eluent, and finally purified to give solid S13 (1.95 mmol, 65%). MALDI-TOF MS: m / z, Calculated: C 48 h 36 BrNSi 2 :761.2; measured value: 761.4.

[0117]

[0118] In a 100ml three-necked flask, S13 ...