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

Patent metadata

Field	Value
Publication number	US-10995069-B2
Application number	US-201716086949-A
Country	US
Kind code	B2
Filing date	Mar 22, 2017
Priority date	Mar 24, 2016
Publication date	May 4, 2021
Grant date	May 4, 2021

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. 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; and a C 6 -C 30 aryloxy group 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; and a C 6 -C 30 aryloxy group; or in case a, b, c, and e are each an integer of 2 or more and d is 2, 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, 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 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; a C 3 -C 20 cycloalkyl group; a C 7 -C 20 arylalkyl group and a 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. The organic electric element according to claim 1 , wherein the first host compound represented by Formula 1 is represented by Formula 3 or 4:

wherein R 1 , R 2 , L 1 , Ar 1 , Ar 2 , Ar 3 , a and b are the same as defined in claim 1 .

3. The organic electric element according to claim 1 , wherein L 1 and L 2 are selected from the group consisting of the following Formulas (A-1) to (A-12):

wherein:
1) a′, c′, d′ and e′ are an integer of 0 to 4, b′ is an integer of 0 to 5, f′ and g′ are an integer of 0 to 3, and h′ is an integer of 0 to 1,
2) R 6 , R 7 and R 8 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; and a C 6 -C 30 aryloxy group;
wherein in case f′ and g′ are an integer of 2 or more, R 6 , R 7 and R 8 are in plural being the same or different from each other, and a plurality of R 6 s or a plurality of R 6 s or plurality of R 8 s may combine to each other to form an aromatic or a heteroaromatic ring, and wherein two adjacent R 6 and R 7 , or R 7 and R 8 may combine to form an aromatic or heteroaromatic ring,
3) Y is NR′, O, S or CR′R″, wherein R′ and R″ are the same as defined above, and
4) Z 1 , Z 2 and Z 3 are independently CR′ or N, and at least one of Z 1 , Z 2 and Z 3 is N.

4. The organic electric element according to claim 1 , wherein the first host compound represented by Formula 1 is represented by any of the following Formulas 5 to 8:

wherein
1) R 1 , R 2 , Ar 1 , Ar 2 , Ar 3 , a, b, R′ and R″ are the same as defined in claim 1 ,
2) R 6 and R 7 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; and a C 6 -C 30 aryloxy group; or in case f′ and g′ are 2 or more, R 6 and R 7 are each in plural being the same or different, and a plurality of R 6 s or a plurality of R 7 s or a plurality of R 8 s or adjacent R 6 and R 7 , or adjacent R 7 and R 8 may combine to each other to form an aromatic or a heteroaromatic ring,
3) a′, c′ and d′ are each an integer of 0 to 4, and f′ and g′ are each an integer of 0 to 3, and
4) Y is NR′, O, S or CR′R″.

5. The organic electric element according to claim 1 , wherein the first host compound represented by Formula 1 is represented by any of the following Formulas 9 to 20:

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

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1051

  with sulfur · CPC title

• C09K2211/1048

  with oxygen · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title