Granted Patent B2

US 12,740,309 · App. 17/953,866 · Granted Sep 15, 2026

Inventors: In-Bum Song (Paju-si, KR); Do-Han Kim (Paju-si, KR); Sung-Jin Park (Paju-si, KR); Jae-Min Moon (Paju-si, KR)

Assignee: LG DISPLAY CO., LTD.

H10K85/342C09K11/06H10K85/633H10K85/636H10K85/654H10K85/6572H10K85/6574H10K85/6576C09K2211/1029C09K2211/185H10K50/13H10K59/12H10K85/626

Abstract

Claims (127)

1 . An organic light emitting diode, comprising:

a first electrode;

a second electrode facing the first electrode; and

a first emitting part including a first red emitting material layer and positioned between the first and second electrodes,

wherein the first red emitting material layer includes a first compound, a second compound and a third compound,

wherein the first compound is represented by Formula 1-1:

wherein in Formula 1-1:

M is molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), 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 3 -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 11 is independently a carbon atom, CR 1 or N;

only one of: a ring (a) with X 3 -X 5 , Y 1 and A; or a ring (b) with 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 6 and X 7 or X 7 and X 8 forms an unsubstituted or substituted C 3 -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 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, 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 forms,

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

X 1 and X 2 or X 2 and X 3 forms an unsubstituted or substituted C 3 -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 hydrogen, 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 3 -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 R 1 , and/or R 2 and R 3 form an unsubstituted or substituted C 3 -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,

wherein the second compound is represented by Formula 2-1:

wherein in Formula 2-1:

each of R 4 , R 5 , R 6 and R 7 is independently selected from the group consisting of hydrogen, protium, deuterium, an unsubstituted or substituted C 1 -C 20 alkyl group and an unsubstituted or substituted C 6 -C 30 aryl group,

each of R 8 and R 9 is independently selected from the group consisting of an unsubstituted or substituted C 6 -C 30 aryl group and an unsubstituted or substituted C 3 -C 30 heteroaryl group,

L 1 is selected from the group consisting of an unsubstituted or substituted C 6 -C 30 arylene group and an unsubstituted or substituted C 3 -C 30 heteroarylene group, and a is 0 or 1,

wherein the third compound is represented by Formula 3-1:

wherein in Formula 3-1:

each of X, Y and Z is independently selected from the group consisting of an unsubstituted or substituted C 6 -C 30 aryl group and an unsubstituted or substituted C 3 -C 30 heteroaryl group;

each of L 2 and L 3 is independently selected from the group consisting of an unsubstituted or substituted C 6 -C 30 arylene group and an unsubstituted or substituted C 3 -C 30 heteroarylene group; and

each of b and c is independently 0 or 1.

2 . The organic light emitting diode of claim 1 , wherein Formula 1-1 is represented by Formula 1-2:

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

wherein Y 3 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 , and

wherein each of M, R,

 m, n, R 1 to R 3 and R a is same as defined in Formula 1-1.

3 . The organic light emitting diode of claim 1 , wherein Formula 1-1 is represented by Formula 1-3:

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

wherein Y 4 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 , and

wherein each of M,

 m, n, R 1 to R 3 and R a is same as defined in Formula 1-1.

4 . The organic light emitting diode of claim 2 , wherein Formula 1-2 is represented by Formula 1-4 or Formula 1-5:

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

wherein each of M, R,

 m, n and R 1 to R 3 is same as defined in Formula 1-1, and X 21 to X 24 and Y 3 is same as defined in Formula 1-2.

5 . The organic light emitting diode of claim 3 , wherein Formula 1-3 is represented by Formula 1-6 or Formula 1-7:

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

wherein each of M,

 m, n, R 1 to R 3 is same as defined in Formula 1-1, and each of X 34 to X 38 and Y 4 is same as defined in Formula 1-3.

6 . The organic light emitting diode of claim 1 , wherein Formula 1-1 is represented by one of Formula 1-8 to Formula 1-11:

wherein R in Formulas 1-8 and 1-9 is same as defined in Formula 1-1,

wherein 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,

wherein each of Y 3 and Y 4 is independently 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 each of R 1 to R 3 and R a is same as defined in Formula 1-1,

wherein each of R 11 to R 13 is independently selected from the group consisting of hydrogen, 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 3 -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 and an unsubstituted or substituted C 3 -C 30 hetero aromatic group,

wherein m is an integer of 1 to 3, and n is an integer of 0 to 2, and

wherein m+n is 3.

7 . The organic light emitting diode of claim 1 , wherein Formula 1-1 is represented by one of Formula 1-12 to Formula 1-15:

wherein R in Formulas 1-12 and 1-13 is same as defined in Formula 1-1,

wherein 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,

wherein each of Y 3 and Y 4 is independently 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 each of R 1 to R 3 and R a is same as defined in Formula 1-1,

wherein each of R 61 to R 64 is independently selected from the group consisting of hydrogen, 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 3 -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 and an unsubstituted or substituted C 3 -C 30 hetero aromatic group,

wherein m is an integer of 1 to 3, and n is an integer of 0 to 2, and

wherein m+n is 3.

8 . The organic light emitting diode of claim 1 , wherein Formula 1-1 is represented by one of Formula 1-16 to Formula 1-19:

wherein R in Formulas 1-16 and 1-17 is same as defined in Formula 1-1,

wherein 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,

wherein each of Y 3 and Y 4 is independently 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 each of R 1 to R 3 and R a is same as defined in Formula 1-1,

wherein each of R 71 to R 73 is independently selected from the group consisting of hydrogen, 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 3 -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 and an unsubstituted or substituted C 3 -C 30 hetero aromatic group,

wherein m is an integer of 1 to 3, and n is an integer of 0 to 2, and

wherein m+n is 3.

9 . The organic light emitting diode of claim 1 , wherein Formula 1-1 is represented by one of Formula 1-20 to Formula 1-23:

wherein R in Formulas 1-20 and 1-21 is same as defined in Formula 1-1,

wherein 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,

wherein each of Y 3 and Y 4 is independently 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 each of R 1 to R 3 and R a is same as defined in Formula 1-1,

wherein each of R 81 to R 85 in Formulas 1-20 to 1-23 is independently selected from the group consisting of hydrogen, 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 3 -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 and an unsubstituted or substituted C 3 -C 30 hetero aromatic group,

wherein m is an integer of 1 to 3, and n is an integer of 0 to 2, and

wherein m+n is 3.

10 . The organic light emitting diode of claim 1 , wherein the first compound is one of the following compounds:

11 . The organic light emitting diode of claim 1 , wherein Formula 2-1 is represented by Formula 2-2 or Formula 2-3:

wherein each of L 1 , a, R 4 to R 9 is same as defined in Formula 2-1.

12 . The organic light emitting diode of claim 1 , wherein the second compound is one of the following compounds:

13 . The organic light emitting diode of claim 1 , wherein Formula 3-1 is represented by Formula 3-2:

wherein X 14 is O or S;

each of Y and Z is independently selected from an unsubstituted or substituted C 6 -C 30 aryl group;

each of L 2 and L 3 is independently selected from an unsubstituted or substituted C 6 -C 30 arylene group; and

each of b and c is independently 0 or 1.

14 . The organic light emitting diode of claim 13 , wherein Formula 3-2 is represented by Formula 3-3:

wherein each of Y and Z is independently selected from phenyl and naphthyl;

each of L 2 and L 3 is independently selected from phenylene and naphthylene; and

each of b and c is independently 0 or 1.

15 . The organic light emitting diode of claim 13 , wherein Formula 3-2 is represented by Formula 3-4:

wherein each of Y and Z is independently selected from phenyl and naphthyl;

each of L2 and L3 is independently selected from phenylene and naphthylene; and

each of b and c is 1.

16 . The organic light emitting diode of claim 1 , wherein Formula 3-1 is represented by Formula 3-5:

wherein each of Y and Z is independently selected from an unsubstituted or substituted C 6 -C 30 aryl group;

each of L 2 and L 3 is independently selected from an unsubstituted or substituted C 6 -C 30 arylene group and an unsubstituted or substituted C 6 -C 30 heteroarylene group;

each of b and c is independently 0 or 1;

each of R 91 to R 98 is independently selected from the group consisting of hydrogen, an unsubstituted or substituted C 1 -C 10 alkyl group and an unsubstituted or substituted C 6 -C 30 aryl group;

optionally, R 91 and R 92 , R 92 and R 93 or R 93 and R 94 form an unsubstituted or substituted C 6 -C 30 aromatic ring.

17 . The organic light emitting diode of claim 1 , wherein the third compound is one of the following compounds:

18 . The organic light emitting diode of claim 1 , wherein each of a weight % of the second and third compounds is greater than a weight % of the first compound.

19 . The organic light emitting diode of claim 1 , further comprising:

a second emitting part including a second red emitting material layer and positioned between the first emitting part and the second electrode; and

a charge generation layer positioned between the first and second emitting parts.

20 . The organic light emitting diode of claim 19 , wherein the second emitting material layer includes a fourth compound represented by Formula 1-1, a fifth compound represented by Formula 2-1 and a sixth compound represented by Formula 3-1.

21 . The organic light emitting diode of claim 1 , further comprising:

a second emitting part including a first blue emitting material layer and positioned between the first electrode and the first emitting part; and

a first charge generation layer positioned between the first and second emitting parts.

22 . The organic light emitting diode of claim 21 , further comprising:

a third emitting part including a second blue emitting material layer and positioned between the first emitting part and the second electrode; and

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

23 . The organic light emitting diode of claim 22 , wherein the first emitting part further includes a green emitting material layer positioned between the red emitting material layer and the second charge generation layer.

24 . The organic light emitting diode of claim 23 , wherein the first emitting part further includes a yellow-green emitting material layer positioned between the red and green emitting material layers.

25 . An organic light emitting device, comprising:

a substrate;

the organic light emitting diode of claim 1 positioned on the substrate.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (11)