IP Library › Granted Patent US 11,744,143
Granted Patent B2
US 11,744,143 · App. 15/672,621 · Granted Aug 29, 2023

Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound

Inventors: Yongsuk Cho (Hwaseong-si, KR); Sangdong Kim (Seoul, KR); Chui Baik (Suwon-si, KR); Hyun Koo (Seoul, KR); Ohyun Kwon (Seoul, KR); Byoungki Choi (Hwaseong-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H10K85/346C07F15/0086C09K11/06H05B33/14C09K2211/1029C09K2211/185H10K50/11H10K2101/10H10K2101/30
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Quick Facts
Patent No.
US 11,744,143
App. No.
15/672,621
Granted
Aug 29, 2023
Kind
B2
Abstract

An organometallic compound represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification.

Claims (46)

1. An organometallic compound represented by one selected from Formulae 1-1 to 1-4:

wherein, in Formulae 1-1 to 1-4,

M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),

X 1 is O or X, and a bond between X 1 and M is a covalent bond,

X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ),

X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), and X 23 is N or C(R 23 ),

X 31 is N or C(R 31 ), X 33 is N or C(R 33 ), X 34 is N or C(R 34 ), X 35 is N or C(R 35 ), X 36 is N or C(R 36 ), and X 37 is N or C(R 37 ),

X 39 is C(R 39a )(R 39b ), N(R 39 ), O, S, Se, or Si(R 39a )(R 39b ),

X 41 is N or C(R 41 ), X 42 is N or C(R 42 ), X 43 is N or C(R 43 ), and X 44 is N or C(R 44 ), provided that the ring of Formulae 1-1 to 1-4 having the X 41 to X 44 groups is not a pyrimidine,

T 1 to T 3 are each independently selected from *—Si(R 5 )(R 6 )—*′, and *—Ge(R 5 )(R 6 )—*′, provided that R 5 and R 6 of *—Si(R 5 )(R 6 )—*′ are not simultaneously phenyl, R 5 and R 6 are linked to each other via a first linking group,

the first linking g coup is selected from a single bond, *—O—*′, *—S—*′, *—C(R 9 )(R 10 )—*′, *—C(R 9 )=*′, *═C(R 9 )—*′, *—C(R 9 )═C(R 10 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—Si(R 9 )(R 10 )—*′, *—Ge(R 9 )(R 10 )—*′, *—B(R 9 )—*′, *—N(R 9 )—*′, and *—P(R 9 )—*′,

b1 to b3 are each independently 0, 1, 2, or 3, provided that the sum of b1 and b2 is at least 1, wherein when b1 is zero, *-(T 1 ) b1 -*′ is a single bond, when b2 is zero, *-(T 2 ) b2 -*′ is a single bond, and when b3 is zero, *-(T 3 ) b3 -*′ is a single bond,

R 5 , R 6 , R 9 , R 10 , R 11 to R 14 , R 21 to R 23 , R 31 , R 33 , R 34 to R 37 , R 39 , R 39a , R 39b and R 41 to R 44 are each independently selected from

hydrogen, deuterium, —F, a cyano group, a nitro group, —SF 5 , a methyl group an ethyl croup, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a text-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-hexyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, are n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an methoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ),

wherein Q 1 to Q 9 are each independently selected from;

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C 1 -C 10 alkyl group, and a phenyl group,

two of R 11 to R 14 may optionally be linked t each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, provided that the condensed ring comprising the ring having the X 11 to X 14 groups and the C 5 -C 30 carbocyclic group fromed by the R 11 to R 14 groups is not a naphthyl group,

two of R 21 to R 23 may optionally be linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,

two of R 34 to R 37 may optionally be linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, and

two of R 41 to R 44 may optionally be linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, provided that the condensed ring comprising the ring having the X 41 to X 44 groups and the C 5 -C 30 carbocyclic group formed by the R 41 to R 44 groups is not a quinoline group,

* and *′ each indicate a binding site to a neighboring atom.

2. The organometallic compound of claim 1 , wherein

b1 is one, and b2 and b3 are each zero;

b2 is one, and b1 and b3 are each zero.

3. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises an emission layer, and

wherein the organic layer comprises at least one of the organometallic compounds of claim 1 .

4. The organic light-emitting device of claim 3 , wherein

the first electrode is an anode,

the second electrode is a cathode, and

the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,

the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

5. The organic light-emitting device of claim 3 , wherein

the emission layer comprises the organometallic compound.

6. The organic light-emitting device of claim 3 , wherein

the emission layer further comprises a host, and

an amount by weight of the host in the emission layer is larger than an amount by weight of the organometallic compound in the emission layer.

7. A diagnostic composition comprising at least one of the organometallic compounds of claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2023
From: CHO, YONGSUK; KIM, SANGDONG; BAIK, CHUL; KOO, HYUN; KWON, OHYUN; CHOI, BYOUNGKI
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 064043/0804 →
Priority Claims (1)
KR 10-2016-0108379 · Aug 25, 2016 · national
Continuity (1)
Related Publication 20180062088A1 · Mar 1, 2018
Cited By (1)
US 12,302,746