Organic electroluminescence device and organometallic compound for organic electroluminescence device
An organic electroluminescence device includes a first electrode, an organic layer disposed on the first electrode, and a second electrode disposed on the organic layer. The organic layer includes an organometallic compound represented by Formula 1 below. where R 1 to R 4 , X 1 to X 4 , Ar 1 to Ar 3 , M, Q, m1 to m4, and n are as defined in the specification.
1. An organic electroluminescence device, comprising:
a first electrode;
an organic layer on the first electrode; and
a second electrode on the organic layer,
wherein the organic layer includes an organometallic compound represented by the following Formula 1:
and
wherein in Formula 1,
M is osmium (Os), iridium (Ir), or platinum (Pt),
Z 1 is 0, S or NR 6 ,
Q is O, S or CH 2 , n is 0 or 1,
X 1 , X 2 , and X 3 are each independently N or C,
X 4 is C,
if n is 0, M is combined with two C atoms and two N atoms,
Ar 1 , Ar 2 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring having 5 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an alkoxy group, an aryloxy group, a cyano group, an amino group, a substituted or unsubstituted silyl group, an alkenyl group, a heteroalkenyl group, an alkynyl group, an unsaturated hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, an acyl group, a carbonyl group, a carbonyl acid, a carbonyl ester, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, a substituted or unsubstituted monovalent non aromatic condensed polycycle, a substituted or unsubstituted monovalent non aromatic condensed heteropolycycle, or may be combined with an adjacent group to form a ring, and
m 1 to m 4 are each independently an integer of 0 to 4.
2. The organic electroluminescence device as claimed in claim 1 , wherein the organic layer includes:
a hole transport region;
an emission layer on the hole transport region; and
an electron transport region on the emission layer, and
the emission layer includes the organometallic compound represented by Formula 1.
3. The organic electroluminescence device as claimed in claim 2 , wherein the emission layer includes a host and a dopant, and
the dopant includes the organometallic compound represented by Formula 1.
4. The organic electroluminescence device as claimed in claim 1 , wherein M is platinum (Pt).
5. The organic electroluminescence device as claimed in claim 1 , wherein Ar 1 to Ar 3 in Formula 1 are each independently phenyl, naphthyl, pyridine, pyrimidine, pyrazine, pyridazine, quinoline, isoquinoline, furan, thiophene, pyrrole, benzofuran, benzothiophene, phenanthryl, phenanthridine, indole, or indazole.
6. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 is represented by one of the following Formula 1-1 to Formula 1-3:
wherein in Formula 1-1 to Formula 1-3,
X 1 and X 3 are each independently N or C, and
Z 1 , Ar 1 , R 1 to R 5 , and m 1 to m 4 are the same as defined in claim 1 , and
in Formula 1-2,
Pt is combined with two C atoms and two N atoms.
7. The organic electroluminescence device as claimed in claim 6 , wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring ring carbon atoms, or combined with an adjacent group to form a ring.
8. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 is represented by one of the following Formula 2-1 to Formula 2-30:
wherein in Formulae 2-1 to 2-30,
X 5 to X 13 are each independently N or CH,
Z 1 , Z 2 and Z 3 are each independently O or S, and
R 1 to R 5 , and m 1 to m 4 are the same as defined in claim 1 .
9. The organic electroluminescence device as claimed in claim 8 , wherein R 1 to R 5 are each independently hydrogen, deuterium, a fluorine atom, a cyano group, a methyl group, an isopropyl group, an isobutyl group, a t-butyl group, a trimethylsilyl group, a triphenylsilyl group, a trifluoromethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzofuran group, or combined with an adjacent group to form a ring.
10. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 is any one selected from compounds in the following Compound Group 3 to Compound Group 5:
11. An organometallic compound represented by the following Formula 1:
wherein in Formula 1,
M is osmium (Os), iridium (Ir), or platinum (Pt),
Z 1 is O, S or NR 6 ,
Q is 0, S or CH 2 , n is 0 or 1,
X 1 , X 2 , and X 3 are each independently N or C,
X 4 is C,
if n is 0, M is combined with two C atoms and two N atoms,
Ar 1 , Ar 2 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring having 5 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an alkoxy group, an aryloxy group, a cyano group, an amino group, a substituted or unsubstituted silyl group, an alkenyl group, a heteroalkenyl group, an alkynyl group, an unsaturated hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, an acyl group, a carbonyl group, a carbonyl acid, a carbonyl ester, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, a substituted or unsubstituted monovalent non aromatic condensed polycycle, or a substituted or unsubstituted monovalent non aromatic condensed heteropolycycle, or may be combined with an adjacent group to form a ring, and
m 1 to m 4 are each independently an integer of 0 to 4.
12. The organometallic compound as claimed in claim 11 , wherein M is platinum (Pt).
13. The organometallic compound as claimed in claim 11 , wherein Ar 1 to Ar 3 in Formula 1 are each independently phenyl, naphthyl, pyridine, pyrimidine, pyrazine, pyridazine, quinoline, isoquinoline, furan, thiophene, pyrrole, benzofuran, benzothiophene, phenanthryl, phenanthridine, indole, or indazole.
14. The organometallic compound as claimed in claim 11 , wherein Formula 1 is represented by one of the following Formula 1-1 to Formula 1-3:
wherein in Formula 1-1 to Formula 1-3,
X 1 and X 3 are each independently N or C, and
Z 1 , Ar 1 , R 1 to R 5 , and m 1 to m 4 are the same as defined in claim 11 , and
in Formula 1-2,
Pt is combined with two C atoms and two N atoms.
15. The organometallic compound as claimed in claim 14 , wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring ring carbon atoms, or combined with an adjacent group to form a ring.
16. The organometallic compound as claimed in claim 11 , wherein Formula 1 is represented by one of the following Formula 2-1 to Formula 2-30:
wherein in Formulae 2-1 to 2-30,
X 5 to X 13 are each independently N or CH,
Z 1 , Z 2 and Z 3 are each independently O or S, and
X 1 , R 1 to R 5 , and m 1 to m 4 are the same as defined in claim 11 .
17. The organometallic compound as claimed in claim 16 , wherein R 1 to R 5 are each independently hydrogen, deuterium, a fluorine atom, a cyano group, a methyl group, an isopropyl group, an isobutyl group, a t-butyl group, a trimethylsilyl group, a triphenylsilyl group, a trifluoromethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzofuran group, or combined with an adjacent group to form a ring.
18. The organometallic compound as claimed in claim 11 , wherein Formula 1 is any one selected from compounds in the following Compound Group 3 to Compound Group 5:
19. The organic electroluminescence device of claim 1 , wherein at least two selected from R 1 to R 4 in Formula 1 is a t-butyl group.