Organic light emitting diode and organic light emitting device including the same
An organic light emitting diode and an organic light emitting device including the same are discussed. The organic light emitting diode can include a first compound represented by a following formula, a second compound as a p-type host, and a third compound as an n-type host in an emitting material layer. As a result, the organic light emitting diode and the organic light emitting device have advantages in the driving voltage, the luminous efficiency and the lifespan.
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 X and Y 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,
R 4 is selected from the group consisting of an unsubstituted or substituted C 1 -C 20 alkyl group and an unsubstituted or substituted C 6 -C 30 aryl group,
a1 is an integer of 0 to 9,
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
a2 is 0 or 1,
wherein the third compound is represented by Formula 3-1:
wherein in Formula 3-1:
X is NR 8 , O or S,
R 8 is selected from the group consisting of an unsubstituted or substituted C 1 -C 10 alkyl group, an unsubstituted or substituted C 6 -C 30 aryl group and an unsubstituted or substituted C 3 -C 30 heteroaryl group,
R 7 is 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 2 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
b is 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, R 1 to R 3 and R a 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 and R a 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 , GOR 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:
wherein
each of X and Y 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,
R 4 is selected from the group consisting of an unsubstituted or substituted C 1 -C 20 alkyl group and an unsubstituted or substituted C 6 -C 30 aryl 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
a2 is 0 or 1.
12 . The organic light emitting diode of claim 1 , wherein Formula 2-1 is represented by Formula 2-3:
wherein
Y is selected from the group consisting of phenyl unsubstituted or substituted with at least one of a C 6 -C 30 aryl group and a C 3 -C 30 heteroaryl group, biphenyl unsubstituted or substituted with at least one of a C 6 -C 30 aryl group and a C 3 -C 30 heteroaryl group and naphthyl unsubstituted or substituted with at least one of a C 6 -C 30 aryl group and a C 3 -C 30 heteroaryl group,
R 4 is selected from the group consisting of an unsubstituted or substituted C 1 -C 20 alkyl group and an unsubstituted or substituted C 6 -C 30 aryl group,
a1 is an integer of 0 to 9,
each of R 5 and R 6 is independently selected from the group consisting of hydrogen and an unsubstituted or substituted C 6 -C 30 aryl group, and optionally R 5 and R 6 form a hetero ring,
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
a2 is 0 or 1.
13 . The organic light emitting diode of claim 1 , wherein the second compound is one of the following compounds:
14 . The organic light emitting diode of claim 1 , wherein Formula 3-1 is represented by Formula 3-2:
wherein
X is NR 8 , O or S,
R 8 is selected from the group consisting of an unsubstituted or substituted C 1 -C 10 alkyl group, an unsubstituted or substituted C 6 -C 30 aryl group and an unsubstituted or substituted C 3 -C 30 heteroaryl group, and
R 7 is 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.
15 . The organic light emitting diode of claim 1 , wherein Formula 3-1 is represented by Formula 3-3:
wherein
X is NR 8 , O or S,
R 8 is selected from the group consisting of an unsubstituted or substituted C 1 -C 10 alkyl group, an unsubstituted or substituted C 6 -C 30 aryl group and an unsubstituted or substituted C 3 -C 30 heteroaryl group,
R 7 is 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 2 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
b is 0 or 1.
16 . The organic light emitting diode of claim 15 , wherein Formula 3-3 is represented by Formula 3-4:
wherein
X is NR 8 , O or S,
R 8 is selected from the group consisting of an unsubstituted or substituted C 1 -C 10 alkyl group, an unsubstituted or substituted C 6 -C 30 aryl group and an unsubstituted or substituted C 3 -C 30 heteroaryl group, and
R 7 is 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.
17 . The organic light emitting diode of claim 1 , wherein Formula 3-1 is represented by Formula 3-5:
wherein
X is NR 8 , O or S,
R 8 is selected from the group consisting of an unsubstituted or substituted C 1 -C 10 alkyl group, an unsubstituted or substituted C 6 -C 30 aryl group and an unsubstituted or substituted C 3 -C 30 heteroaryl group,
R 7 is 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 2 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
b is 0 or 1.
18 . The organic light emitting diode of claim 17 , wherein Formula 3-5 is represented by Formula 3-6:
wherein
X is NR 8 , O or S,
R 8 is selected from the group consisting of an unsubstituted or substituted C 1 -C 10 alkyl group, an unsubstituted or substituted C 6 -C 30 aryl group and an unsubstituted or substituted C 3 -C 30 heteroaryl group, and
R 7 is 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.
19 . The organic light emitting diode of claim 1 , wherein the third compound is one of the following compounds:
20 . 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.
21 . 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.
22 . The organic light emitting diode of claim 21 , 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.
23 . 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.
24 . The organic light emitting diode of claim 23 , 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.
25 . The organic light emitting diode of claim 24 , 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.
26 . The organic light emitting diode of claim 25 , wherein the first emitting part further includes a yellow-green emitting material layer positioned between the red and green emitting material layers.
27 . An organic light emitting device, comprising:
a substrate;
the organic light emitting diode of claim 1 positioned on the substrate.