Compound for organic electric element, organic electric element comprising the same and electronic device thereof

Patent metadata

Field	Value
Publication number	US-10797247-B2
Application number	US-201715836306-A
Country	US
Kind code	B2
Filing date	Dec 8, 2017
Priority date	Jul 24, 2014
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

Provided are an organic electric elements, and electronic devices thereof, wherein high luminous efficiency, low driving voltage and the improved lifetime of the organic electronic element are achieved by using the compound of the present invention as a phosphorescent host material.

First claim

The invention claimed is:

1. A compound of Formula 1 below:

wherein,
1) A ring is C 10 aryl group,
2) B ring is selected from the group consisting of the following formulas B-1 to B-16:

in formulas B-1 to B-16, “*” indicates the position to be condensed with pyrazine comprising two Ns,
3) W 1 and W 2 are each independently a single bond, S or O,
4) V is N or C,
5) X is O or S,
6) a is an integer of 0 to 6, b and c are each an integer of 0 to 4, d is an integer of 0 to 11,
7) R 1 , R 2 , R 3 and R 4 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C 6 -C 60 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxyl group and -L′-N(R a )(R b ),
or when a, b and c are 2 or more, R 1 , R 2 and R 3 are each in plural and are the same or different, and a plurity of R 1 , a plurity of R 2 , or a plurity of R 3 may be bonded to each other to form a ring,
8) L′ is selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene group, a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, and a C 2 -C 60 heterocyclic group, and R a and R b are each independently selected from the group consisting of a C 6 -C 60 aryl group, a fluorenyl group, a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, and a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P,
9) L 1 is each independently selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene group, a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, and a C 2 -C 60 heterocyclic group and
the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxyl group, and aryloxy group may be each optionally further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group substituted or unsubstituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, -L′-N(R a )(R b ), a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -C 20 aryl group, a C 6 -C 20 aryl group substituted with deuterium, a fluorenyl group, a C 2 -C 20 heterocyclic group, a C 3 -C 20 cycloalkyl group, a C 7 -C 20 arylalkyl group, and a C 8 -C 20 arylalkenyl group, and these substituents may be linked each other to form a ring, wherein ‘ring’ comprises a C 3 -C 60 aliphatic ring, a C 6 -C 60 aromatic ring, a C 2 -C 60 heterocyclic group or the combination thereof.

2. The compound of claim 1 , wherein Formula 1 above is represented by any one of Formulas 2 to 4 below:

in Formulas 2 to 4, X, L 1 , Ar 1 , R 1 , R 2 , R 3 , a, b and c are the same as defined in claim 1 .

3. The compound of claim 1 , wherein Formula 1 above is represented by any one of Formulas 5 to 7 below:

in Formulas 5 to 7, X, L 1 , Ar 1 , R 1 , R 2 , R 3 , R 4 , a, b, c, d and B ring are the same as defined in claim 1 .

4. The compound of claim 1 , wherein the chemical structure Ar t of the formula 1 comprising the pyrazine is represented by any one of the following Formulas C-1 to C-22:

in Formulas C-1 to C-22, R 4 is the same as defined in claim 1 , and d is an integer of 0 to 11.

5. The compound of claim 1 , wherein R 4 of Formula 1 is represented by any one of the following formulas R-1 to R-10:

in Formulas R-1 to R-10,
1) Q 1 to Q 15 are each independently CR g or N,
2) W 1 is S, O or NR h ,
3) W 2 to W 4 are each independently S, O, NR h or CR i R j ,
4) R e is selected from the group consisting of hydrogen, deuterium, halogen, a silane group substituted or unsubstituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -C 20 aryl group, a C 6 -C 20 aryl group substituted with deuterium, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20 cycloalkyl group, a C 7 -C 20 arylalkyl group, and a C 8 -C 20 arylalkenyl group, and when these substituents are adjacent, they may be linked each other to form a ring,
5) R f and R g are each independently selected from the group consisting of hydrogen, deuterium, a C 6 -C 20 aryl group, a fluorenyl group, a fused ring group of a C 3 -C 20 aliphatic ring and a C 6 -C 20 aromatic ring, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, and a C 1 -C 30 alkoxyl group,
6) R h , R i and R j are each independently selected from the group consisting of a C 6 -C 20 aryl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 1 -C 20 alkoxyl group and a fluorenyl group, R i and R j may be linked each other to form a spiro compound together with C to which they are bonded,
7) q is each independently an integer of 0 to 5,
8) r is each independently an integer of 0 to 4,
9) s is each independently an integer of 0 to 3,
when q, r and s are each 2 or more, R e is each the same or different, and * indicates the position to be bonded.

6. The compound of claim 1 , wherein Formula 1 is any one of the compounds below:

Assignees

• Duk San Neolux Co Ltd

Inventors

• Lee Bumsung
• Lee Sunhee
• Mun Soungyun
• Kim Daesung
• Park Jungcheol
• Lee Yunsuk
• Yeo Seungwon
• Park Junghwan
• Kim Wonsam
• Choi Yeon Hee

Classifications

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title