Compound for organic electric element, organic electric element using same, and electronic device comprising same

Patent metadata

Field	Value
Publication number	US-2019106390-A1
Application number	US-201716086949-A
Country	US
Kind code	A1
Filing date	Mar 22, 2017
Priority date	Mar 3, 2016
Publication date	Apr 11, 2019
Grant date	—

Abstract

Provided are an organic electric element and an electronic device thereof comprising a mixture of the compounds of Formula 1 and Formula 2 as a phosphorescent host material, and thereby obtaining high light emission efficiency, low driving voltage, and improved lifetime.

First claim

What is claimed is:

1 . A compound represented by Formula 2 below:

wherein
1) Ar 4 is 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; 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 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 hetero atom of O, N, S, Si, or P,
2) c and e are integer of 0 to 10, and d is an integer of 0 to 2,
3) R 3 , R 4 and R 5 are the same or different from each other, and are each independently selected from the group consisting of a deuterium; a 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 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; and -L′-N(R a )(R b ) wherein L′, R a and R b are the same as defined above; or in case c and e are 2 or more and d is 2, R 3 , R 4 and R 5 are each in plural being the same or different, and a plurality of R 1 s or a plurality of R 2 s or a plurality of R 3 s or a plurality of R 4 s or a plurality of R 5 s may combine to each other to form a ring.
4) L 2 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;
5) A and B are independently a C 6 -C 60 aryl group or a C 2 -C 20 heterocyclic group, and when both A and B are a substituted or unsubstituted C 6 aryl group (phenyl group), d is 2 and R 4 s combine to each other to form a ring to form an aromatic or hetero ring,
6) i and j are independently 0 or 1, with the proviso that i+j is 1 or more, and when i or j is 0, it means a direct bond,
7) X 1 and X 2 are independently NR′, O, S, or CR′R″, wherein R′ and R″ are 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; or R′ and R″ may combine to each other to form a spiro,
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 ) wherein L′, R a and R b are the same as defined above; 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 a C 3 -C 60 aliphatic ring or a C 6 -C 60 aromatic ring or a C 2 -C 60 heterocyclic ring or a fused ring formed by the combination thereof.

2 . 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 wherein the emitting layer comprises 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; 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, or P, wherein Ar 2 and Ar 3 may combine to each other to form a ring,
2) a is an integer of 0 to 4, b is an integer of 0 to 3, c and e are integer of 0 to 10, and d is an integer of 0 to 2,
3) R 1 , R 2 , R 3 , R 4 and R 5 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 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; and -L′-N(R a )(R b ) wherein L′, R a and R b are the same as defined above; or in case a, b, c, and e are each an integer of 2 or more, d is 2 and R 1 , R 2 , R 3 , R 4 and R 5 are each in plural being the same or different, and a plurality of R 1 s or a plurality of R 2 s or a plurality of R 3 s or a plurality of R 4 s or a plurality of R 5 s may combine to each other to form a ring,
4) L 1 and L 2 are 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,
5) A and B are each independently a C 6 -C 60 aryl group or a C 2 -C 20 heterocyclic group, wherein both A and B are a substituted or unsubstituted C 6 aryl group (phenyl group), d is 2 and R 4 s combine to each other to form an aromatic or hetero ring,
6) i and j are independently 0 or 1, with the proviso that i+j is 1 or more, and when i or j is 0, it means a direct bond,
7) X 1 and X 2 are independently NR′, O, S, or CR′R″, wherein R′ and R″ are 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 wherein R′ and R″ may combine to each other to form a spiro,
8) n is an integer of 1 or 2, and when n is 2, two Ar 2 s are the same or different from each other, and two Ar 3 s are each the same or different from each other.
wherein, the aryl group, fluorenyl group, arylene group, het

Assignees

• Duk San Neolux Co Ltd

Inventors

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

Classifications

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• H01L51/0072

  Electricity · mapped topic

• C07D491/048

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

• C07D487/04 Primary

  Ortho-condensed systems · CPC title