Granted Patent B2

US 12,679,857 · App. 17/505,865 · Granted Jul 14, 2026

Inventors: Jae-Min Moon (Paju-si, KR); Sung-Jin Park (Paju-si, KR); Hye-Seung Kang (Paju-si, KR); Yoo-Jeong Jeong (Paju-si, KR)

Assignee: LG Display Co., Ltd.

C07F15/0033H10K85/342H10K50/11H10K2101/10H10K2101/30H10K2101/40

Abstract

Claims (124)

1 . An organic metal compound having the following structure of Formula 1:

wherein

M is molybdenum (Mo), tungsten (W), rhenium (Re), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) or silver (Ag);

each of A and B is a carbon atom;

R is an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 1 -C 20 alkyl silyl group, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 hetero alicyclic group, an unsubstituted or substituted C 6 -C 30 aromatic group or an unsubstituted or substituted C 3 -C 30 hetero aromatic group;

each of X 1 to X 2 , X 4 , X 5 , X 6 , X 7 and X 9 to X 11 is independently CR 1 or N;

only one of: a ring (a) with X 3 -X 5 , Y 1 and A; or a ring (b) with and X 8 -X 11 , Y 2 and B is formed; and

if the ring (a) is formed,

each of X 3 and Y 1 is a carbon atom,

X 8 is CR 1 or N,

X 6 and X 7 or X 7 and X 8 forms an unsubstituted or substituted C 4 -C 30 alicyclic ring, the unsubstituted or substituted C 3 -C 30 hetero alicyclic ring, an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring; and

Y 2 is BR 2 , CR 2 R 3 , C═O, SiR 2 R 3 , GeR 2 R 3 , PR 2 , P═O, O, S, SO 2 , Se, SeO 2 , Te or TeO 2 , or NR a wherein R a is an unsubstituted or substituted C 1 -C 20 alkyl group or an unsubstituted or substituted C 6 -C 30 aromatic group;

if the ring (b) is formed,

each of X 8 and Y 2 is a carbon atom,

X 3 is CR 1 or N,

X 1 and X 2 or X 2 and X 3 forms an unsubstituted or substituted C 4 -C 30 alicyclic ring, an unsubstituted or substituted C 3 -C 30 hetero alicyclic ring, an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring; and

Y 1 is BR 2 , CR 2 R 3 , C═O, SiR 2 R 3 , GeR 2 R 3 , PR 2 , P═O, O, S, SO 2 , Se, SeO 2 , Te TeO 2 , or NR a wherein R a is an unsubstituted or substituted C 1 -C 20 alkyl group or an unsubstituted or substituted C 6 -C 30 aromatic group,

each of R 1 to R 3 is independently protium, deuterium, tritium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrozone group, an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 2 -C 20 alkenyl group, an unsubstituted or substituted C 2 -C 20 alkynyl group, an unsubstituted or substituted C 1 -C 20 alkoxy group, an amino group, an unsubstituted or substituted C 1 -C 20 alkyl amino group, an unsubstituted or substituted C 1 -C 20 alkyl silyl group, a carboxyl group, a nitrile group, an isonitrile group, a sulfanyl group, a phosphino group, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 hetero alicyclic group, an unsubstituted or substituted C 6 -C 30 aromatic group or an unsubstituted or substituted C 3 -C 30 hetero aromatic group,

optionally,

two adjacent carbons to which R 1 is attached, and/or

R 2 and R 3

form an unsubstituted or substituted C 4 -C 30 alicyclic ring, an unsubstituted or substituted C 3 -C 30 hetero alicyclic ring, an unsubstituted or substituted C 6 -C 30 aromatic ring or an unsubstituted or substituted C 3 -C 30 hetero aromatic ring;

 is an auxiliary ligand;

m is an integer of 1 to 3;

n is an integer of 0 to 2; and

m+n is an oxidation number of M.

2 . The organic metal compound of claim 1 , having the following structure of Formula 2:

wherein

each of M, R,

 m and n is a same as defined in Formula 1;

each of X 21 to X 27 is independently CR 1 or N;

Y 3 is BR 2 , CH 2 , CR 2 R 3 , C═O, SiR 2 R 3 , GeR 2 R 3 , PR 2 , P═O, O, S, SO 2 , Se, SeO 2 , Te or TeO 2 ; each of R 1 to R 3 is a same as defined in Formula 1.

3 . The organic metal compound of claim 1 , having the following structure of Formula 3:

wherein

each of M,

 m and n is a same as defined in Formula 1;

each of X 31 to X 38 is independently CR 1 or N;

Y 4 is BR 2 , C, CR 2 R 3 , C═O, SiR 2 R 3 , GeR 2 R 3 , PR 2 , P═O, O, S, SO 2 , Se, SeO 2 , Te or TeO 2 ; and

each of R 1 to R 3 is a same as defined in Formula 1.

4 . The organic metal compound of claim 2 , having the following structure of Formula 4 or Formula 5:

wherein

each of M, R,

 m, n, X 21 to X 24 and Y 3 is a same as defined in Formula 2;

each of X 41 to X 45 is independently CR 1 or N; and

each of R 1 to R 3 is a same as defined in Formula 1.

5 . The organic metal compound of claim 3 , having the following structure of Formula 6 or Formula 7:

wherein

M,

 m, n, X 34 to X 38 and Y 4 is a same as defined in Formula 3;

each of X 51 to X 55 is independently CR 1 or N;

each of R 1 to R 3 is a same as defined in Formula 1.

6 . The organic metal compound of claim 1 , having a structure of any one of Formula 8 to Formula 11:

wherein

R is a same as defined in Formula 1;

each of X 21 to X 24 , X 34 to X 38 , X 41 to X 45 and X 51 to X 55 is independently CR 1 or N;

each of Y 3 and Y 4 is independently BR 2 , CH 2 , CR 2 R 3 , C═O, SiR 2 R 3 , GeR 2 R 3 , PR 2 , P═O, O, S, SO 2 , Se, SeO 2 , Te or TeO 2 ;

each of R 1 to R 3 is a same as defined in Formula 1;

each of R 11 to R 13 is independently protium, deuterium, tritium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrozone group, an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 2 -C 20 alkenyl group, an unsubstituted or substituted C 2 -C 20 alkynyl group, an unsubstituted or substituted C 1 -C 20 alkoxy group, an amino group, an unsubstituted or substituted C 1 -C 20 alkyl amino group, an unsubstituted or substituted C 1 -C 20 alkyl silyl group, a carboxyl group, a nitrile group, an isonitrile group, a sulfanyl group, a phosphino group, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 hetero alicyclic group, an unsubstituted or substituted C 6 -C 30 aromatic group or an unsubstituted or substituted C 3 -C 30 hetero aromatic group;

m is an integer of 1 to 3; and

n is an integer of 0 to 2;

m+n is 3.

7 . The organic metal compound of claim 1 , wherein the organic metal compound is selected form the following compounds:

8 . The organic metal compound of claim 1 , wherein the organic metal compound is selected from the following compounds:

9 . The organic metal compound of claim 1 , wherein the organic metal compound is selected form the following compounds:

10 . The organic metal compound of claim 1 , wherein the organic metal compound is selected from the following compounds:

11 . The organic metal compound of claim 1 , wherein the organic metal compound is selected from the following compounds:

12 . An organic light emitting device, comprising:

a substrate; and

an organic light emitting diode on the substrate and including:

a first electrode;

a second electrode facing the first electrode; and

an emissive layer disposed between the first and second electrodes and including at least one emitting material layer,

wherein the at least one emitting material layer includes the organic metal compound having the structure of Formula 1 according to claim 1 .

13 . The organic light emitting device of claim 12 , wherein the organic metal compound has the following structure of Formula 2

wherein

each of M, R,

 m and n is a same as defined in Formula 1;

each of X 21 to X 27 is independently CR 1 or N; Y 3 is BR 2 , CH 2 , CR 2 R 3 , C═O, SiR 2 R 3 , GeR 2 R 3 , PR 2 , P═O, O, S, SO 2 , Se, SeO 2 , Te or TeO 2 ; and

each of R 1 to R 3 is a same as defined in Formula 1.

14 . The organic light emitting device of claim 12 , wherein the organic metal compound has the following structure of Formula 3:

wherein

each of M, R,

 m and n is a same as defined in Formula 1;

each of X 31 to X 38 is independently CR 1 or N;

Y 4 is BR 2 , C, CR 2 R 3 , C═O, SiR 2 R 3 , GeR 2 R 3 , PR 2 , P═O, O, S, SO 2 , Se, SeO 2 , Te or TeO 2 ; and

each of R 1 to R 3 is a same as defined in Formula 1.

15 . The organic light emitting device of claim 13 , wherein the organic metal compound has the following structure of Formula 4 or Formula 5:

wherein

each of M, R,

 m, n, X 21 to X 24 and Y 3 is a same as defined in Formula 2;

each of X 41 to X 45 is independently CR 1 or N; and

each of R 1 to R 3 is a same as defined in Formula 1.

16 . The organic light emitting device of claim 14 , wherein the organic metal compound has the following structure of Formula 6 or Formula 7:

wherein

M, R,

 m, n, X 34 to X 38 and Y 4 is a same as defined in Formula 3;

each of X 51 to X 55 is independently CR 1 or N; and

each of R 1 to R 3 is a same as defined in Formula 1.

17 . The organic light emitting device of claim 12 , wherein the organic metal compound has any one of the following structures of Formula 8 to Formula 11:

wherein

R is a same as defined in Formula 1;

each of X 21 to X 24 , X 34 to X 38 , X 41 to X 45 and X 51 to X 55 is independently CR 1 or N;

each of Y 3 and Y 4 is independently BR 2 , CH 2 , CR 2 R 3 , C═O, SiR 2 R 3 , GeR 2 R 3 , PR 2 , P═O, O, S, SO 2 , Se, SeO 2 , Te or TeO 2 ;

each of R 1 to R 3 is a same as defined in Formula 1;

each of R 11 to R 13 is independently protium, deuterium, tritium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrozone group, an unsubstituted or substituted C 1 -C 20 alkyl group, an unsubstituted or substituted C 2 -C 20 alkenyl group, an unsubstituted or substituted C 2 -C 20 alkynyl group, an unsubstituted or substituted C 1 -C 20 alkoxy group, an amino group, an unsubstituted or substituted C 1 -C 20 alkyl amino group, an unsubstituted or substituted C 1 -C 20 alkyl silyl group, a carboxyl group, a nitrile group, an isonitrile group, a sulfanyl group, a phosphino group, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 hetero alicyclic group, an unsubstituted or substituted C 6 -C 30 aromatic group or an unsubstituted or substituted C 3 -C 30 hetero aromatic group;

m is an integer of 1 to 3; and

n is an integer of 0 to 2,

m+n is 3.

18 . The organic light emitting device of claim 12 , wherein the at least one emitting material layer includes a host and a dopant, and the dopant includes the organic metal compound.

19 . The organic light emitting device of claim 12 , wherein

the at least one emitting material layer includes a first emitting material layer and a second emitting material layer;

the emissive layer includes:

a first emitting part disposed between the first and second electrodes, and including the first emitting material layer;

a second emitting part disposed between the first emitting part and the second electrode, and including the second emitting material layer; and

a first charge generation layer disposed between the first and second emitting parts,

wherein at least one of the first emitting material layer or the second emitting material layer includes the organic metal compound.

20 . The organic light emitting device of claim 19 ,

wherein the second emitting material layer includes:

a lower emitting material layer disposed between the first charge generation layer and the second electrode; and

an upper emitting material layer disposed between the lower emitting material layer and the second electrode,

wherein one of the lower emitting material layer or the upper emitting material layer includes the organic metal compound, and

wherein the emissive layer further includes:

a third emitting part disposed between the second emitting part and the second electrode, and including a third emitting material layer; and

a second charge generation layer disposed between the second and third emitting parts.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (17)