Organic compound having improved luminescent properties, organic light emitting diode and organic light emitting device having the compound

Patent metadata

Field	Value
Publication number	US-11401268-B2
Application number	US-201916715699-A
Country	US
Kind code	B2
Filing date	Dec 16, 2019
Priority date	Dec 28, 2018
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

An organic compound, an organic light emitting diode including the compound, and an organic light emitting device including the organic light emitting diode are disclosed. The organic compound may include a fused hetero aromatic moiety having a p-type property and an aza-acridine moiety having an n-type property bonded to the fused hetero aromatic moiety via an aromatic or a hetero aromatic linker. The organic compound has relatively high energy level since it includes plural fused hetero aromatic rings. Holes and electrons can be recombined in an emitting material layer in a balanced manner since the organic compound has a bipolar property. The organic light emitting diode and the organic light emitting device including the organic compound have enhanced luminous efficiency and luminous lifetime.

First claim

The invention claimed is:

1. An organic compound having the structure of Chemical Formula 1:

wherein:
each of R 1 and R 2 is independently protium, deuterium, tritium, linear or branched C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 30 aryl group or C 4 -C 30 hetero aryl group, or R 1 and R 2 form a C 5 -C 30 spiro structure;
each R 3 is independently protium, deuterium, tritium, linear or branched C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 30 aryl group or C 4 -C 30 hetero aryl group, or adjacent two groups among R 3 form C 4 -C 20 fused aromatic or hetero aromatic ring; o is an integer from 0 to 4;
wherein X 2 is a nitrogen atom (N);
each of X 1 , X 3 and X 4 is independently CR 4 or nitrogen atom (N), wherein at least one of X 1 to X 4 is nitrogen atom, wherein R 4 is protium, deuterium, tritium, linear or branched C 1 -C 20 alkyl group, C 1 C 20 alkoxy group, C 6 -C 30 aryl group or C 4 -C 30 hetero aryl group, or adjacent two groups among R 4 form C 4 -C 30 fused aromatic or hetero aromatic ring; and
each of Y 1 to Y 5 is independently CR 5 or nitrogen atom (N), wherein at least three of Y 1 to Y 5 is CR 5 , wherein R 5 is protium, deuterium, tritium, linear or branched C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group or C 10 -C 30 fused group of a heterocycle ring and an aryl group, wherein the C 10 -C 30 fused group of a heterocycle ring and an aryl group is unsubstituted or substituted with a group selected from the group consisting of linear or branched C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 30 aryl group, C 4 -C 30 hetero aryl group, C 4 -C 30 aromatic or hetero aromatic amino group and a combination thereof, fused with a C 4 -C 20 aromatic or hetero aromatic ring or linked by a spiro structure of a C 4 -C 20 aromatic or hetero aromatic ring, wherein at least one R 5 among Y 1 to Y 5 is C 10 -C 30 fused group of a heterocycle ring and an aryl group unsubstituted or substituted with a group selected from the group consisting of linear or branched C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 30 aryl group, C 4 -C 30 hetero aryl group, C 4 -C 30 aromatic or hetero aromatic amino group and a combination thereof, fused with a C 4 -C 20 aromatic or hetero aromatic ring or linked by a spiro structure of a C 4 -C 20 aromatic or hetero aromatic ring.

2. The organic compound of claim 1 , wherein the C 10 -C 30 fused group of a heterocycle ring and an aryl group constituting R 5 includes at least one nitrogen atom (N).

3. The organic compound of claim 1 , wherein the C 10 -C 30 fused group of a heterocycle ring and an aryl group constituting R 5 is selected from the group consisting of carbazolyl, acridinyl, carbolinyl, spirofluorenocarbazolyl, spirofluorenoacridinyl, phenazinyl, phenoxazinyl and phenothiazinyl, and wherein each of the carbazolyl, the acridinyl, the carbolinyl, the spirofluorenocarbazolyl, the spirofluorenoacridinyl, the phenazinyl, the phenoxazinyl and the phenothiazinyl is independently unsubstitued or substituted with a group selected from the group consisting of linear or branched C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 30 aryl group, C 4 -C 30 hetero aryl group, C 4 -C 30 aromatic or hetero aromatic amino group and a combination thereof, fused with a C 4 -C 20 aromatic or hetero aromatic ring or linked by a spiro structure of a C 4 -C 20 aromatic or hetero aromatic ring, respectively.

4. The organic compound of claim 1 , having the structure of Chemical Formula 2:

wherein:
each of R 11 and R 12 is independently linear or branched C 1 -C 20 lalkyl group or C 6 -C 20 aryl group;
each of R 13 and R 14 is independently protium, deuterium, tritium or linear or branched C 1 -C 20 alkyl group; o is an integer from 0 to 4; p is an integer from 1 to 3;
each of R 15 to R 18 is independently protium, deuterium, tritium, linear or branched C 1 -C 20 alkyl group or C 10 -C 30 fused group of a heterocycle ring and an aryl group having at least one nitrogen atom (N) on a ring, wherein the C 10 -C 30 fused group of a heterocycle ring and an aryl group is unsubstituted or substituted a group selected from the group consisting of linear or branched C 1 -C 20 alkyl group, C 6 -C 30 aryl group, C 4 -C 30 hetero aryl group, C 4 -C 30 aromatic or hetero aromatic amino group and a combination thereof, wherein at least one of R 15 to R 18 is C 10 -C 30 fused group of a heterocycle ring and an aryl group having at least one nitrogen atom (N) on the ring, wherein the C 10 -C 30 fused group of a heterocycle ring and an aryl group is unsubstituted or substituted with a group selected from the group consisting of linear or branched C 1 -C 20 alkyl group, C 6 -C 30 aryl group, C 4 -C 30 hetero aryl group, C 4 -C 30 aromatic or hetero aromatic amino group and a combination thereof;
Y is nitrogen atom (N) or CR 19 , wherein R 19 is protium, deuterium, tritium or linear or branched C 1 -C 20 alkyl group.

5. The organic compound of claim 1 , having the structure of Chemical Formula 3:

6. An organic lightemitting diode, comprising:
a first electrode;
a second electrode facing the first electrode;
at least one emitting unit disposed between the first and second electrodes and wherein
the at least one emitting unit comprises an emitting material layer,
wherein the emitting material layer comprises an organic compound having the structure of Chemical Formula 1:

wh

Assignees

• Lg Display Co Ltd
• Univ Korea Res & Bus Found

Inventors

• Seo Bo-Min
• Yoon Dae-Wi
• Yang Joong-Hwan
• Choi Dong-Hoon
• Choi Su-Na
• Kim Hyung-Jong
• Godumala Mallesham

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title