Compound for organic electronic device, organic electronic device using same, and electronic apparatus thereof

Patent metadata

Field	Value
Publication number	US-11299452-B2
Application number	US-201716302920-A
Country	US
Kind code	B2
Filing date	May 18, 2017
Priority date	May 19, 2016
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

Abstract

Provided are an organic electric element comprising as a phosphorescent host material, a mixture of the compounds of Formula (1) and Formula (2), and an organic electronic device or apparatus thereof for achieving a high luminous efficiency, a low driving voltage, and an improved lifespan.

First claim

What is claimed is:

1. An organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,
wherein the organic material layer comprises an emitting layer, and the emitting layer is a phosphorescent light emitting layer comprising a first host compound represented by Formula (1) and a second host compound represented by Formula (2):

wherein:
1) Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently selected from the group consisting of a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one hetero atom of O, N, S, Si or 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 aryloxy group;
2) c and e are each independently integers of 0 to 10, d is an integer of 0 to 2, and R 3 , R 4 and R 5 are, being the same or different from each other, each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom 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 60 aryloxy group; and -L′-N(R a )(R b ) (wherein 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, and R a and R b are 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 hetero atom of O, N, S, Si, and P), wherein in case c and e are 2 or more, R 3 , R 4 and R 5 are each in plural being the same or different and a plurality of R 3 or a plurality of R 4 or a plurality of R 5 combine to each other to form a ring;
3) L 1 , L 2 , L 3 and L 4 are each independently selected from the group consisting of a single bond; a C 6 -C 60 arylene group; and 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;
4) A and B are each independently a C 6 -C 20 aryl group or a C 2 -C 20 heterocyclic group;
5) i and j are each independently 0 or 1, wherein i+j is 1 or more, and where i or j is 0, it means a direct bond,
6) X 1 and X 2 are each independently O, S, or CR′R″, wherein R′ and R″ are each independently hydrogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 3 -C 60 heterocyclic group; or a C 1 -C 50 alkyl group, and R′ and R″ are optionally combine to each other to form a spiro ring,
wherein the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted with C 1 -C 20 alkyl group or C 6 -C 20 aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; -L′-N(R a )(R b ); a C 1 -C 20 alkylthio group; C 1 -C 20 alkoxyl group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 20 aryl group; C 6 -C 20 aryl group substituted with deuterium; a fluorenyl group; C 2 -C 20 heterocyclic group; C 3 -C 20 cycloalkyl group; C 7 -C 20 arylalkyl group; and C 8 -C 20 arylalkenyl group, wherein the substituents may combine each other and form a saturated or unsaturated ring, wherein the term ‘ring’ means C 3 -C 60 aliphatic ring or C 6 -C 60 aromatic ring or a C 2 -C 60 heterocyclic ring or a fused ring formed by the combination of thereof, and
wherein the compound of Formula (2) excludes a compound wherein both A and B are a C 6 aryl group.

2. The organic electric element according to claim 1 , wherein the first host compound represented by Formula (1) is represented by any one of the following Formulas (3) to (5):

wherein:
1) L 1 , L 3 , L 4 , Are and Ara are the same as defined in the claim,
2) X 3 is O or S,
3) a is an integer of 0 to 4, b is an integer of 0 to 3, and R 1 and R 2 are the same or different from each other and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom 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 aryloxy group; and -L′-N(R a )(R b ); or in case a and b are 2 or more, R 1 and R 2 are each in plural being the same or different, and a plurality of R 1 or a plurality of R 2 combine to each other to form a ring.

3. The organic electric element according to claim 1 , wherein the compound represented by Formula (1) is represented by any one of the following Formulas (6) to (14):

wherein:
1) L 1 , L 3 , L 4 , Are and Ara are the same as defined in the claim,
2) a is an integer of 0 to 4, b is an integer of 0 to 3, and R 1 and R 2 are the same or different from each other, and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si and P; a fused ring group of a C 3 -C 6 o 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 aryloxy group; and -L′-N(R a )(R b ); or in case a and b are 2 or more, R 1 and R 2 are each in plural being the same or different, and a plurality of R 1 or a plurality of R 2 combine to each other to form a ring.

4. The organic electric element according to claim 1 , wherein the first host compound represented by Formula (1) is represented by any one of the following Formulas (15) to (23):

wherein:
1) L 1 , L 3 , L 4 , Ar 2 and Ara are the same as defined in claim 1 ,
2) a is an integer of 0 to 4, b is an integer of 0 to 3, and R 1 and R 2 are the same or different from each other, and are each independently selected from the group consisting of deuterium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom 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 aryloxy group; and -L′-N(R a )(R b ); o

Assignees

• Duk San Neolux Co Ltd

Inventors

• Lee Mun Jae
• Mun Soung Yun
• Kwon Jae Taek
• Kim Dae Sung
• Park Moo Jin
• Park Chi Hyun
• Lee Sun Hee
• Song Hyun Ju
• Lee Bum Sung

Classifications

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D491/048

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

• C07D333/50

  condensed with carbocyclic rings or ring systems · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title