US2018309070A1PendingUtilityA1
Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound
Assignee: SAMSUNG ELECTRONICS CO LTDPriority: Apr 20, 2017Filed: Jan 15, 2018Published: Oct 25, 2018
Est. expiryApr 20, 2037(~10.7 yrs left)· nominal 20-yr term from priority
Inventors:Jungin LeeKyuyoung HwangSoyeon KimSeongjun YoonSunghun LeeHyeonho ChoiByoungki ChoiYoonhyun Kwak
C09K 11/06H01L 51/0072C09K 11/025H01L 51/0094C07F 15/0086H01L 51/0087H01L 51/5206H10K 85/346C09K 2211/1044C09K 2211/185C09K 2211/1029G01N 21/64C07F 19/00H10K 50/15H10K 50/81H10K 85/40H10K 50/171H10K 2101/10H10K 50/82H10K 50/11H10K 50/18H10K 50/16H10K 85/6572H10K 50/17
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Claims
Abstract
An organometallic compound represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An organometallic compound represented by Formula 1:
Formula 1
wherein, in Formula 1,
X 51 is selected from O, S, and N(R 51 ),
R 11 to R 14 , R 21 to R 23 , R 31 to R 33 , R 41 to R 44 , and R 51 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ),
when X 51 is O or S, at least one of R 11 to R 14 , R 21 to R 23 , R 31 to R 33 , and R 41 to R 44 is —Si(Q 3 )(Q 4 )(Q 5 ),
when X 51 is N(R 51 ), at least one of R 11 to R 14 , R 21 to R 23 , R 31 to R 33 , R 41 to R 44 , and R 51 is —Si(Q 3 )(Q 4 )(Q 5 ),
at least one substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, and the substituted C 1 -C 60 alkoxy group is selected from:
deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), and —P(═O)(Q 18 )(Q 19 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), and —P(═O)(Q 28 )(Q 29 ); and
—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), and —P(═O)(Q 38 )(Q 39 ), and
Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 1 -C 60 alkyl group substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryl group substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
2 . The organometallic compound of claim 1 , wherein
X 51 is N(R 51 ).
3 . The organometallic compound of claim 1 , wherein
R 11 to R 14 , R 21 to R 23 , R 31 to R 33 , R 41 to R 44 , and R 51 are each independently selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF 5 , a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group; a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl 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, and a pyrimidinyl 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 ), and 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 isopentyl 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 isopentyl 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.
4 . The organometallic compound of claim 1 , wherein
R 11 to R 14 , R 21 to R 23 , R 31 to R 33 , R 41 to R 44 , and R 51 are each independently selected from: hydrogen, deuterium, —F, a cyano group, a nitro group, —SF 5 , a methyl group, an ethyl group, 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 isopentyl 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 ethoxy group, a propoxy group, a butoxy group, and a pentoxy group; a methyl group, an ethyl group, 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 isopentyl 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 ethoxy group, a propoxy group, a butoxy group, and a pentoxy 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, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group; and —Si(Q 3 )(Q 4 )(Q 5 ), and Q 3 to Q 5 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 isopentyl group, a sec-pentyl group, and a tert-pentyl 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 isopentyl group, a sec-pentyl group, and a tert-pentyl group, each substituted with at least one selected from deuterium and a C 1 -C 10 alkyl group.
5 . The organometallic compound of claim 1 , wherein
R 11 to R 14 , R 21 to R 23 , R 31 to R 33 , R 41 to R 44 , and R 51 are each independently selected from hydrogen, deuterium, —F, a cyano group, a nitro group, —SF 5 , —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , groups represented by Formulae 9-1 to 9-19, and —Si(Q 3 )(Q 4 )(Q 5 ), and Q 3 to Q 5 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, —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 isopentyl group, a sec-pentyl group, and a tert-pentyl group:
wherein * in Formulae 9-1 to 9-19 indicates a binding site to a neighboring atom.
6 . The organometallic compound of claim 1 , wherein
Q 3 to Q 5 in —Si(Q 3 )(Q 4 )(Q 5 ) are identical to one another.
7 . The organometallic compound of claim 1 , wherein
one or two of R 11 to R 14 , R 21 to R 23 , R 31 to R 33 , and R 41 to R 44 are —Si(Q 3 )(Q 4 )(Q 5 ).
8 . The organometallic compound of claim 1 , wherein
at least one of R 21 to R 23 is —Si(Q 3 )(Q 4 )(Q 5 ); at least one of R 41 to R 44 is —Si(Q 3 )(Q 4 )(Q 5 ); or at least one of R 21 to R 23 is —Si(Q 3 )(Q 4 )(Q 5 ), and at least one of R 41 to R 44 is —Si(Q 3 )(Q 4 )(Q 5 ).
9 . The organometallic compound of claim 1 , wherein
one or two of R 22 , R 42 , and R 43 are —Si(Q 3 )(Q 4 )(Q 5 ).
10 . The organometallic compound of claim 1 , wherein
at least one of R 11 to R 13 , R 22 , R 32 , R 42 , and R 43 is not hydrogen.
11 . The organometallic compound of claim 1 , wherein
the organometallic compound is represented by one of Formulae 1-1 to 1-8:
wherein, in Formulae 1-1 to 1-8,
R 11 to R 13 , R 22 , R 32 , R 42 , and R 43 are the same as described in claim 1 , provided that R 11 to R 13 and R 32 are not hydrogen, and
at least one of R 22 , R 42 , and R 43 is —Si(Q 3 )(Q 4 )(Q 5 ).
12 . The organometallic compound of claim 11 , wherein
R 22 is —Si(Q 3 )(Q 4 )(Q 5 ), one of R 42 and R 43 is —Si(Q 3 )(Q 4 )(Q 5 ); or R 22 is —Si(Q 3 )(Q 4 )(Q 5 ), and one of R 42 and R 43 is —Si(Q 3 )(Q 4 )(Q 5 ).
13 . The organometallic compound of claim 1 , wherein
the organometallic compound is one of Compounds 1 to 256:
wherein TMS in Compounds 1 to 256 indicates a trimethylsilyl group.
14 . 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 at least one organometallic compound of claim 1 .
15 . The organic light-emitting device of claim 14 , 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, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
16 . The organic light-emitting device of claim 14 , wherein
the emission layer comprises the organometallic compound.
17 . The organic light-emitting device of claim 16 , wherein
the emission layer further comprises a host, wherein an amount of the host in the emission layer is larger than an amount of the organometallic compound in the emission layer.
18 . The organic light-emitting device of claim 17 , wherein
the amount of the organometallic compound in the emission layer is in a range of 0.01 parts by weight to 15 parts by weight based on 100 parts by weight of the emission layer.
19 . The organic light-emitting device of claim 17 , wherein
the host comprises a carbazole-containing compound.
20 . A diagnostic composition comprising at least one organometallic compound of claim 1 .Join the waitlist — get patent alerts
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