Heterocyclic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
US-2024373662-A1 · Nov 7, 2024 · US
US9692000B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9692000-B2 |
| Application number | US-201313895780-A |
| Country | US |
| Kind code | B2 |
| Filing date | May 16, 2013 |
| Priority date | Mar 23, 2006 |
| Publication date | Jun 27, 2017 |
| Grant date | Jun 27, 2017 |
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Disclosed is an organic electroluminescent element having high luminous efficiency and long life. Also disclosed are a display device and an illuminating device respectively using such an organic electroluminescent element. Specifically disclosed is an organic electroluminescent element comprising an electrode and at least one or more organic layers on a substrate. This organic electroluminescent element is characterized in that at least one of the organic layers is a light-emitting layer containing a phosphorescent compound and a host compound, the phosphorescent compound has a HOMO of −5.15 to −3.50 eV and a LUMO of from −1.25 to +1.00 eV, and the host compound has a 0-0 band of the phosphorescence spectrum at not more than 460 nm and a glass transition temperature of not less than 60° C.
Opening claim text (preview).
What is claimed is: 1. An organic electroluminescent element comprising a substrate having thereon an electrode and at least one organic layer, wherein at least one of the organic layers is a light-emitting layer containing a phosphorescent compound and a host compound represented by Formula (7), wherein R 1 and R 2 each represent a hydrogen atom or a substituent, and Ra represents a hydrogen atom or a substituent selected from the group consisting of: an alkyl group, a cycloalkyl group, a phenyl group, an imidazolyl group, a pyridyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, an isothiazolyl group, a thienyl group, a dibenzofuryl group, a dibenzothienyl group, a carbolinyl group, a morpholyl group, a methoxy group, an ethoxy group, a propyloxy group, a pentyloxy group, a hexyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a phenoxy group, a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, a hydroxy group, a mercapto group, and a silyl group; n1, n2, and na each are an integer of 0-4; and X represents 0, and the phosphorescent compound has a HOMO of from −5.15 to −3.50 eV and a LUMO of from −1.25 to +1.00 eV, and the host compound has a 0-0 band of 460 nm or less in a phosphorescence spectrum and the host compound has a glass transition temperature of 90° C. or more; and the phosphorescent compound is represented by Formula (A), wherein, in Formula (A), R 1 represents a substituent; Z represents a group of non-metal elements necessary to form a five-to-seven-membered ring; n1 is an integer of 0 to 5; B 1 -B 5 each represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom, and at least one of them represents a nitrogen atom; M 1 is a metal of 8-10 group in the periodic table; X 1 and X 2 each represent a carbon atom, a nitrogen atom or an oxygen atom; L 1 is a group of elements forming ligands having coordination number 2 with X 1 and X 2 ; L 1 is an integer of 1 to 3; m2 is an integer of 0 to 2; and m1+m2 is 2 or 3. 2. The organic electroluminescent element of claim 1 , wherein the phosphorescent compound has the HOMO of from −4.80 to −3.50 eV and the LUMO of from −0.80 to +1.00 eV. 3. The organic electroluminescent element of claim 1 , wherein m2 is 0 in the phosphorescent compound represented by Formula (A). 4. The organic electroluminescent element of claim 1 , wherein a nitrogen containing heterocyclic ring formed by B 1 to B 5 is an imidazole ring in the phosphorescent compound represented by Formula (A). 5. The organic electroluminescent element of claim 1 , wherein Formula (A) is further represented by Formula (B), wherein R 1 , R 2 and R 3 each represent a substituent; Z represents a group of non-metal elements necessary to form a five- to seven-membered ring; n1 is an integer of 0 to 5; M 1 is a metal of 8-10 group in the periodic series; X 1 and X 2 each are a carbon atom, a nitrogen atom or an oxygen atom; L 1 is a group of elements forming ligands having coordination number 2 with X 1 and X 2 ; m1 is an integer of 1 to 3; m2 is an integer of 0 to 2; and m1+m2 is 2 or 3. 6. The organic electroluminescent element of claim 5 , wherein the substituent R 2 in Formula (B) is further represented by Formula (C), wherein R 4 represents a substituent having a steric parameter (Es value) of −0.5 or less; R 5 represents a substituent; n5 is an integer of 0 to 4; and (*) in Formula represents a bonding position. 7. The organic electroluminescent element of claim 1 , wherein a glass transition temperature of the host compound is 130° C. or more. 8. The organic electroluminescent element of claim 1 , wherein a glass transition point of the host compound is 160° C. or more. 9. The organic electroluminescent element of claim 1 , further comprising an electron inhibition layer. 10. The organic electroluminescent element of claim 1 , emitting white light. 11. A display device comprising the organic electroluminescent element of claim 1 . 12. An illuminating device comprising the organic electroluminescent element of claim 1 .
containing one nitrogen atom as the heteroatom · CPC title
Heterocyclic compounds · CPC title
Electroluminescent · CPC title
containing organic luminescent materials · CPC title
of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title
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