[0063] Taking Example 1 as an example, the synthetic route is as follows:
[0064]
[0065] Embodiment one:
[0066] Step 1) Preparation of Intermediate-1:
[0067] Throw in 40.0g (0.17mol) 4,6-dichloro-2-phenyl-5-aminopurine, 54.1g (0.17mol) 4,6-diphenyl-2-(4-aminophenyl)-1, 3,5-Triazine as the raw material, 1.926g (0.0017mol) tetrakistriphenylphosphorous palladium, 48.0g (0.5mol) sodium tert-butoxide, and 500.0g xylene, heated to 100-110°C, kept the temperature for 9hrs, Cool down to room temperature, add 300.0g of water, separate layers, desolventize the organic phase to obtain 98.3g of brown oily liquid, and obtain 18.6g (0.035mol) of Intermediate-1 by column chromatography;
[0068] Step 2) Preparation of Intermediate-2:
[0069] Add 18.6g (0.035mol) of intermediate-1 and 4.95g (0.035mol) of benzoyl chloride, 300.0g of DMF and 95.0g of silica gel loaded with ferric chloride (the content of aluminum chloride is 9%, about 0.053mol) , raised the temperature to 100-110°C, kept the reaction for 7.0 hr, cooled to room temperature, filtered with suction, and desolvated the filtrate to obtain the crude product of Intermediate-2, and obtained 12.3g (0.20mol) of the fine product of Intermediate-2 by column chromatography.
[0070] Step 3) preparation of product TM-1:
[0071] Drop into 12.3g (0.20mol) intermediate-2, 3.56g (0.21mol) diphenylamine, 0.232g (0.0002mol) tetrakis triphenyl phosphopalladium, 5.8g (0.06mol) sodium tert-butoxide and 180g dimethylbenzene, heat up to 100-110°C, react for 10 hours, cool down to room temperature, add 100.0g of water, separate layers, and desolventize the organic phase to obtain the crude product of TM-1, and obtain 12.5g (0.017mol) of fine product TM-1 by column chromatography. Using HPLC-MS to identify the compound, formula C 50 h 34 N 8 , detection value [M+1] + =747.95, calculated value 746.86.
[0072] For the sublimation of the compound structure TM-1, weigh 10.0g of the fine product of the compound structure TM-1, and put it in a vacuum sublimation instrument, the sublimation parameter is the sublimation vacuum degree 2×10 -5 Pa, the temperature of the sublimation zone 3 is 295°C, the temperature of the sublimation zone 2 is 180°C, and the temperature of the sublimation zone 1 is 125°C. The set temperature is a gradient temperature rise, which increases by 50°C every 15 minutes. After reaching the target temperature, heat preservation and sublimation After 5.0 hours, a total of 9.0 g of fine product was obtained by sublimation, HPLC: 99.9%, and the sublimation yield was 90.0%.
[0073] The preparation of embodiment two to twelve
[0074] The reaction formula of embodiment two to twelve is as follows:
[0075]
[0076]
[0077] Embodiment 2 to embodiment 12 are all the same as the experimental process of embodiment 1, and the raw materials are replaced according to the following table to obtain embodiment 2-embodiment 12:
[0078] Embodiment and raw material corresponding table are as follows:
[0079] Table II:
[0080]
[0081]
[0082]
[0083] According to the method described in Example 1 of compound sample preparation, novel organic optoelectronic materials (Example 1 to Example 12) were prepared, and the relevant compound HPLC-MSMS data are as follows:
[0084] Table 3: HPLC-MS detection data
[0085]
[0086] The organic electroluminescent device can be prepared according to the methods in the art, and the specific method is: under high vacuum conditions, sequentially vapor-deposit MoO on the cleaned conductive glass (indium tin oxide) substrate 3 , hole transport layer, light emitting layer, BCP, electron transport layer, 1nm LiF and 120nm Al. produced by this method figure 1 The shown device can be divided into: Embodiment 1, Embodiment 2, Embodiment 3, and Embodiment 4 as a light-emitting layer according to different functional layers of the device; Embodiment 5, Embodiment 6, and Embodiment 4 as a hole transport layer. Embodiment 7, Embodiment 8; Embodiment 9, Embodiment 10, Embodiment 11, Embodiment 12 as the electron transport layer.
[0087] Example as light-emitting layer
[0088] Device Embodiment 1
[0089] ITO/MoO 3 (10nm)/NPB(50nm)/compound structure TM-1:Ir(piq)2:(acac)(6wt%, 30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm) .
[0090] Device embodiment two
[0091] ITO/MoO 3 (10nm)/NPB(50nm)/compound structure TM-2: Ir(piq)2:(acac)(6wt%, 30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm) .
[0092] Device Embodiment Three
[0093] ITO/MoO 3 (10nm)/NPB(50nm)/compound structure TM-3: Ir(piq)2:(acac)(6wt%, 30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm) .
[0094] Device Embodiment Four
[0095] ITO/MoO 3 (10nm)/NPB(50nm)/compound structure TM-4: Ir(piq)2:(acac)(6wt%, 30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm) .
[0096] Example as hole transport layer
[0097] Device Embodiment Five
[0098] ITO/MoO 3 (10nm)/compound structure TM-5(30nm)/Alq 3 (30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm).
[0099] Device Embodiment Six
[0100] ITO/MoO 3 (10nm)/compound structure TM-6(30nm)/Alq 3 (30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm).
[0101] Device Embodiment Seven
[0102] ITO/MoO 3 (10nm)/compound structure TM-7(30nm)/Alq 3 (30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm).
[0103] Device Embodiment Eight
[0104] ITO/MoO 3 (10nm)/compound structure TM-8(30nm)/Alq 3 (30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm).
[0105] Example as an electron transport layer
[0106] Device Embodiment Nine
[0107] ITO/MoO 3 (10nm)/NPB(50nm)/Alq 3 (30nm)/BCP(10nm)/compound structure TM-9(30nm)/LiF(1nm)/Al(120nm).
[0108] Device Embodiment Ten
[0109] ITO/MoO 3 (10nm)/NPB(50nm)/Alq 3 (30nm)/BCP(10nm)/compound structure TM-10(30nm)/LiF(1nm)/Al(120nm).
[0110] Device Embodiment Eleven
[0111] ITO/MoO 3 (10nm)/NPB(50nm)/Alq 3 (30nm)/BCP(10nm)/compound structure TM-11(30nm)/LiF(1nm)/Al(120nm).
[0112] Device Embodiment Twelve
[0113] ITO/MoO 3 (10nm)/NPB(50nm)/Alq 3 (30nm)/BCP(10nm)/compound structure TM-12(30nm)/LiF(1nm)/Al(120nm).
[0114] Device Comparison Example 1
[0115] ITO/MoO 3 (10nm)/NPB(50nm)/Alq 3 (30nm)/BCP(10nm)/TPBI(30nm)/LiF(1nm)/Al(120nm).
[0116]The current-brightness-voltage characteristics of the device are completed by a keithley source measurement system (keithley236 source measure unit) with a corrected silicon photodiode, and the performance data of the device are shown in Table 4.
[0117] Table 4: Device Performance Data
[0118]
[0119]
[0120] Device Embodiment 1 to Device Embodiment 4 prepared with the compound of the present invention as the main material all emit red light, the highest current efficiency reaches 7.5cd/A, and the highest brightness can reach 12749cd/m2. Efficiency and other aspects have obvious advantages. As an electron and/or hole transport material, it can obviously reduce the driving voltage of the device and improve the efficiency of the device.
