IP Library › Granted Patent US 10,916,715
Granted Patent B2
US 10,916,715 · App. 15/789,749 · Granted Feb 9, 2021

Organometallic compound and organic light-emitting device including the same

Inventors: Soobyung Ko (Yongin-si, KR); Sungbum Kim (Yongin-si, KR); Youngkook Kim (Yongin-si, KR); Heechoon Ahn (Yongin-si, KR); Mieun Jun (Yongin-si, KR); Seokhwan Hwang (Yongin-si, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/0085H01L51/0067H01L51/0087C07D213/61C07D213/89C07D249/10H01L51/5016
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Quick Facts
Patent No.
US 10,916,715
App. No.
15/789,749
Granted
Feb 9, 2021
Kind
B2
Abstract

An organometallic compound and an organic light-emitting device including the same are provided. The organometallic compound has Formula 1: wherein M is a third row transition metal, L 1 is a ligand represented by Formula 2A and n1 is 1, 2, or 3, L 2 is a ligand represented by Formula 2B and n2 is 0, 1, or 2. When n1 is two or more, two or more L 1 (s) are identical to or different from each other. When n2 is two or more, two or more L 2 (s) are identical to or different from each other. Details about Formula 2A and Formula 2B are provided.

Claims (117)

1. An organometallic compound represented by Formula 1:

wherein M in Formula 1 is a third row transition metal,

in Formula 1, L 1 is a ligand represented by Formula 2A, and n1 is 1, 2, or 3, wherein, when n1 is two or more, two or more L 1 (s) are identical to or different from each other,

in Formula 1, L 2 is a ligand represented by Formula 2B, and n2 is 0, 1, or 2, wherein, when n2 is two or more, two or more L 2 (s) are identical to or different from each other,

the sum of n1 and n2 in Formula 1 is two or three,

* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1,

in Formula 2A, X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), and X 3 is N or C(R 3 ),

in Formula 2B, Y 1 is carbon, Y 2 and Y 3 are each independently carbon or nitrogen, Y 4 is nitrogen, a bond between Y 1 and Y 2 is a single bond or a double bond, a bond between Y 2 and Y 3 is a single bond, and a bond between Y 3 and Y 4 is a single bond or a double bond,

ring A 1 and ring A 2 in Formula 2B are each a C 2 -C 60 heterocyclic group comprising at least one N as a ring-forming atom,

in Formulae 2A and 2B, R 1 to R 3 , R 5 , R 6 , R 11 , and R 12 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),

R 4 is an electron withdrawing group,

R 2 and R 3 in Formula 2A are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group,

R 5 and R 6 in Formula 2A are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group,

two neighboring groups of a plurality of R 11 (s) in Formula 2B are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group,

two neighboring groups of a plurality of R 12 (s) in Formula 2B are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group,

neighboring R 11 and R 12 in Formula 2B are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group,

a11 and a12 in Formula 2B are each independently an integer from 0 to 10, and

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, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 60 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C 4 -C 60 carbocyclic group, and the substituted C 2 -C 60 heterocyclic group is selected from:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 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 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );

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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 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, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ), and

—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 1 -C 60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C 6 -C 60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group.

2. The organometallic compound of claim 1 , wherein

M in Formula 1 is iridium or osmium and the sum of n1 and n2 is three; or

M in Formula 1 is platinum and the sum of n1 and n2 is two.

3. The organometallic compound of claim 1 , wherein

in Formula 2A, X 1 is C(R 1 ), X 2 is C(R 2 ), and X 3 is C(R 3 ); or

in Formula 2A, X 1 is C(R 1 ), X 2 is N, and X 3 is C(R 3 ).

4. The organometallic compound of claim 1 , wherein,

in Formula 2A, X 3 is C(R 3 ) and R 3 is an electron withdrawing group.

5. The organometallic compound of claim 1 , wherein

ring A 1 and ring A 2 in Formula 2B are each independently a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazol group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazol group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

6. The organometallic compound of claim 1 , wherein

R 1 to R 3 , R 5 , R 6 , R 11 , and R 12 in Formulae 2A and 2B are each independently selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, and a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl 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 , —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 );

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 fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl 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 fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl 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 hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 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, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ); and

—Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ), and

Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 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 20 aryl group, a C 1 -C 20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C 1 -C 20 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group;

a C 6 -C 20 aryl group substituted with at least one selected from deuterium, —F, and a cyano group; and

a biphenyl group and a terphenyl group.

7. The organometallic compound of claim 1 , wherein,

in Formula 2B, the sum of a11 and a12 is equal to or greater than one, and at least one selected from R 11 and R 12 is an electron withdrawing group.

8. The organometallic compound of claim 1 , wherein

the electron withdrawing group is —F, —Cl, —Br, —I, a cyano group, a nitro group, or —B(Q 1 )(Q 2 ); or a first group substituted with at least one selected from —F, —Cl, —Br, —I, —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, and —B(Q 31 )(Q 32 ),

provided that the first group is selected from:

a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, and a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, and a C 1 -C 20 alkoxy group, each substituted with at least one selected from deuterium, —CD 3 , —CD 2 H, —CDH 2 , a hydroxyl group, an amidino group, a hydrazino group, a hydrazono 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, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 );

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 fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

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 fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, —CD 3 , —CD 2 H, —CDH 2 , a hydroxyl group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 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, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and

Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 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 20 aryl group, a C 1 -C 20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C 1 -C 20 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group;

a C 6 -C 20 aryl group substituted with at least one selected from deuterium, —F, and a cyano group; and

a biphenyl group and a terphenyl group.

9. The organometallic compound of claim 1 , wherein

the electron withdrawing group is —F, —Cl, —Br, —I, a cyano group, a nitro group, or —B(Q 1 )(Q 2 ); or a first group substituted with at least one selected from —F, —Cl, —Br, —I, —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, and —B(Q 31 )(Q 32 ),

provided that the first group is selected from:

a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, and a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, and a C 1 -C 20 alkoxy group, each substituted with at least one selected from deuterium, —CD 3 , —CD 2 H, —CDH 2 , 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;

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, and a fluorenyl group; and

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, and a fluorenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 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, a cycloheptenyl group, a phenyl group, a naphthyl group, and a fluorenyl group, and

Q 1 , Q 2 , Q 31 , and Q 32 are each independently selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group;

a C 1 -C 20 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group;

a phenyl group and a naphthyl group, each substituted with at least one selected from deuterium, —F, and a cyano group; and

a biphenyl group and a terphenyl group.

10. The organometallic compound of claim 1 , wherein

L 2 is a ligand selected from groups represented by Formulae 2B-1 to 2B-60:

wherein, in Formulae 2B-1 to 2B-60,

Z 1 and Z 2 are the same as described in connection with R 11 and R 12 in claim 1 , respectively,

d2 is an integer from 0 to 2,

d3 is an integer from 0 to 3,

d4 is an integer from 0 to 4,

d6 is an integer from 0 to 6, and

* and *′ each indicate a binding site to M in Formula 1.

11. The organometallic compound of claim 1 , wherein

L 2 is a ligand selected from groups represented by Formula 2B-A:

wherein, in Formula 2B-A,

Z 1a , Z 1b , and Z 1c are the same as described in connection with R 11 in claim 1 ,

ring A 2 is a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group,

R 12 and a12 are the same as described in claim 1 , and

* and *′ each indicate a binding site to M in Formula 1.

12. The organometallic compound of claim 11 , wherein

at least one selected from Z 1a and Z 1b is an electron withdrawing group.

13. The organometallic compound of claim 1 , wherein

L 2 is a ligand selected from groups represented by Formulae 2B(1) to 2B(8):

wherein, in Formulae 2B(1) and 2B(8),

Z 1a and Z 1b are the same as described in connection with R 11 in claim 1 ,

Z 2 is the same as described with R 12 in claim 1 , and

* and *′ each indicate a binding site to M in Formula 1.

14. The organometallic compound of claim 1 , wherein

the organometallic compound is selected from Compounds 1 to 96:

15. The organometallic compound of claim 1 , wherein

the organometallic compound emits blue light having a maximum emission wavelength of about 445 nm to about 465 nm.

16. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrode, the organic layer including an emission layer,

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

17. The organic light-emitting device of claim 16 , wherein

the first electrode is an anode,

the second electrode is a cathode,

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

the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary 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.

18. The organic light-emitting device of claim 16 , wherein

the organometallic compound is comprised in the emission layer, the emission layer further comprises a host, and an amount of the host in the emission layer is larger than an amount of the organometallic compound in the emission layer.

19. The organic light-emitting device of claim 18 , wherein

the host comprises at least one selected from a silicon-containing compound and a phosphine oxide-containing compound.

20. The organic light-emitting device of claim 17 , wherein

the hole transport region comprises a p-dopant, of which a lowest unoccupied molecular orbital (LUMO) energy level is lower than −3.5 eV.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2017
From: KO, SOOBYUNG; KIM, SUNGBUM; KIM, YOUNGKOOK; AHN, HEECHOON; JUN, MIEUN; HWANG, SEOKHWAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 043917/0171 →
Priority Claims (1)
KR 10-2016-0136575 · Oct 20, 2016 · national
Continuity (1)
Related Publication 20180114927A1 · Apr 26, 2018
Cited By (6)
US 12,225,816 US 12,279,519 US 12,520,719 US 12,674,091 US 12,685,016 US 12,751,199