Novel compound and organic light-emitting device including same
A technology of organic light-emitting devices and compounds, applied in the field of novel compounds and organic light-emitting devices containing them, can solve problems such as high driving voltage, low efficiency, and short life, and achieve high color purity, long life, and high efficiency.
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no. 1 approach
[0035] The first embodiment of the present invention provides a compound represented by the following chemical formula 1:
[0036] chemical formula 1
[0037]
[0038] In Chemical Formula 1,
[0039] Ar is substituted or unsubstituted C 6 -C 30 Aryl, or substituted or unsubstituted C 5 -C 30 heteroaryl,
[0040] R 1 to R 3 Each independently represents hydrogen, deuterium, substituted or unsubstituted C 1 -C 6 Alkyl, substituted or unsubstituted C 6 ~C 30 Aryl, or substituted or unsubstituted C 5 ~C 30 heteroaryl,
[0041] L 1 and L 2 Each independently represents straight chain or substituted or unsubstituted C 5 -C 30 Arylene,
[0042] H is hydrogen.
[0043] In an example of the present invention, in the compound of the above chemical formula 1, L can be connected at the first position, the third position or the fourth position of spirobifluorene 1 . Attach L to the first, third or fourth position of spirobifluorene 1Since the compound with the stru...
preparation example 1
[0097] Preparation Example 1: Synthesis of Intermediate IA
[0098]
[0099] For the synthesis of the desired compound, the preparation of intermediate IA was carried out through the above steps.
[0100] The synthesis method of the following IA1 is as follows.
[0101]
[0102] In a round bottom flask, 36.6g of 2-bromonaphthyl, 44.4g of 9,9-dimethyl-9H-fluoren-2-amine, 33.9g of t-BuONa, Pd 2 (dba) 3 3.2g, (t-Bu) 3 1.7 ml of P was dissolved in 350 ml of toluene, followed by reflux stirring. The reaction was confirmed by thin layer chromatography (TLC), and the reaction was terminated by adding water. The organic layer was extracted with dichloromethane (MC) and filtered under reduced pressure, followed by column purification and recrystallization to obtain IA1g (yield 84%).
[0103] IA2 to IA9 were synthesized by the same method as above IA1, using different starting materials X1 and X2.
[0104]
Synthetic example 1
[0105] Synthesis Example 1: Synthesis of Compound 1
[0106]
[0107] In a round bottom flask, 5.0 g of 3-bromo-9,9'-spirobis[fluorene], 7.0 g of IA1, 2.2 g of t-BuONa, Pd 2 (dba) 3 0.6g, (t-Bu) 3 After 0.7 ml of P was dissolved in 50 ml of toluene, stirring was performed under reflux. The reaction was confirmed by thin layer chromatography (TLC), and the reaction was terminated by adding water. The organic layer was extracted with dichloromethane (MC) and filtered under reduced pressure, followed by column purification and recrystallization to obtain 6.5 g of Compound 1 (yield 67%).
[0108] m / z: 649.28 (100.0%), 650.28 (54.5%), 651.28 (14.5%), 652.29 (2.5%)
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