Novel compound and organic light-emitting element comprising same

Abstract

A compound of the present invention has: an HOMO energy level facilitating hole injection; a high LUMO energy level capable of blocking electrons; and excellent hole transport characteristics. When applied to a hole injection layer or a hole transport layer of an organic light emitting device, the compound enables the organic light emitting device to have stability and durability resulted from excellent low voltages, high efficiency, and high Tg.

Description

technical field

[0001] The present invention relates to novel compounds and organic light-emitting elements comprising them. Background technique

[0002] Recently, self-illuminating organic light-emitting elements that can be driven at low voltages have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs) that are the mainstream of flat panel display elements. Lightweight and thin, it is also advantageous in terms of power consumption, and the color reproduction range is wide, so it is attracting attention as a next-generation display element.

[0003] Materials used as organic layers in organic light-emitting devices can be roughly classified into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials according to their functions.

[0004] Amine derivatives having a carbazole skeleton have been extensively studied as hole transport materials used i...

Examples

Embodiment 1

[0132] Embodiment 1: the synthesis of compound 1

[0133]

[0134] In a round bottom flask, 2.5 g of Intermediate A, 3.08 g of bis([1,1'-biphenyl]-4-yl)amine, 1.15 g of t-BuONa, 0.3 g of Pd 2 (dba) 3 , 0.4ml of (t-Bu) 3 P was dissolved in 60ml of toluene, and then stirred under reflux. The reaction was confirmed by TLC, and water was added, and then the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and purified on a column to obtain 2.56 g of compound 1 (yield 58%).

[0135] m / z: 553.24 (100.0%), 554.24 (44.8%), 555.25 (9.8%), 556.25 (1.5%)

Embodiment 2

[0136] Embodiment 2: the synthesis of compound 2

[0137]

[0138] Use N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine to replace the bis([1,1'- Biphenyl]-4-yl)amine, and compound 2 was synthesized by the same method as compound 1.

[0139] m / z: 593.27 (100.0%), 594.28 (48.0%), 595.28 (11.5%), 596.28 (1.9%)

Embodiment 3

[0140] Embodiment 3: the synthesis of compound 3

[0141]

[0142]Use N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine to replace the two ([1 ,1'-biphenyl]-4-yl)amine, and compound 3 was synthesized by the same method as compound 1.

[0143] m / z: 629.27 (100.0%), 630.28 (51.3%), 631.28 (13.1%), 632.28 (2.3%)

technical field

[0001] The present invention relates to novel compounds and organic light-emitting elements comprising them. Background technique

[0002] Recently, self-illuminating organic light-emitting elements that can be driven at low voltages have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs) that are the mainstream of flat panel display elements. Lightweight and thin, it is also advantageous in terms of power consumption, and the color reproduction range is wide, so it is attracting attention as a next-generation display element.

[0003] Materials used as organic layers in organic light-emitting devices can be roughly classified into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials according to their functions.

[0004] Amine derivatives having a carbazole skeleton have been extensively studied as hole transport materials used i...

Examples

Embodiment 1

[0132] Embodiment 1: the synthesis of compound 1

[0133]

[0134] In a round bottom flask, 2.5 g of Intermediate A, 3.08 g of bis([1,1'-biphenyl]-4-yl)amine, 1.15 g of t-BuONa, 0.3 g of Pd 2 (dba) 3 , 0.4ml of (t-Bu) 3 P was dissolved in 60ml of toluene, and then stirred under reflux. The reaction was confirmed by TLC, and water was added, and then the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and purified on a column to obtain 2.56 g of compound 1 (yield 58%).

[0135] m / z: 553.24 (100.0%), 554.24 (44.8%), 555.25 (9.8%), 556.25 (1.5%)

Embodiment 2

[0136] Embodiment 2: the synthesis of compound 2

[0137]

[0138] Use N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine to replace the bis([1,1'- Biphenyl]-4-yl)amine, and compound 2 was synthesized by the same method as compound 1.

[0139] m / z: 593.27 (100.0%), 594.28 (48.0%), 595.28 (11.5%), 596.28 (1.9%)

Embodiment 3

[0140] Embodiment 3: the synthesis of compound 3

[0141]

[0142]Use N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine to replace the two ([1 ,1'-biphenyl]-4-yl)amine, and compound 3 was synthesized by the same method as compound 1.

[0143] m / z: 629.27 (100.0%), 630.28 (51.3%), 631.28 (13.1%), 632.28 (2.3%)

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