Organic electroluminescent element, and illumination device and display device each comprising the element

Patent metadata

Field	Value
Publication number	US-9617255-B2
Application number	US-201013145842-A
Country	US
Kind code	B2
Filing date	Jan 21, 2010
Priority date	Feb 6, 2009
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

Provided is an o organic electroluminescence element comprising an anode, a cathode and a plurality of composing layers including a light emitting layer sandwiched between the anode and the cathode, wherein an electron transport layer containing the compound represented by Formula (1) is included in the composing layers; the light emitting layer contains a phosphorescence emitting organic metal complex; and the cathode or one composing layer adjacent to the cathode contains a metal or a metal compound belonging to Group 1 or Group 2 of the periodic table of elements, provided that the metal exhibits a standard electrode potential larger than −3 V vs. SHE in a system of the metal ion (M n+ )/the metal (M):

First claim

The invention claimed is:

1. An organic electroluminescence element comprising an anode, a cathode and a plurality of composing layers including a light emitting layer sandwiched between the anode and the cathode,
wherein an electron transport layer containing a compound represented by any one of Formulas (2) to (4) is included in the composing layers; the light emitting layer contains a phosphorescence emitting organic metal complex; and the cathode or one composing layer adjacent to the cathode contains a metal or a metal compound belonging to Group 1 or Group 2 of the periodic table of elements, provided that the metal exhibits a standard electrode potential larger than −3 V vs. SHE in a system of the metal ion (M n+ )/the metal (M):

wherein R11 to R17 each represent a hydrogen atom or a substituent; X represents —S—; and X11 to X17 represents —C(R18)=, or —N═, R18 represents a hydrogen atom or a substituent, and when a plurality of —C(R18)= exists, the plurality of R18s may be the same or different, provided that at least one of R11 to R18 represents a benzene ring having a substituent of an aromatic hydrocarbon ring group or an aromatic heterocyclic group;

wherein R21 to R27 each represent a hydrogen atom or a substituent; X21 to X23, and X26 to X28 each represent —C(R28)=, or —N═; X24 and X25 each represent —C(R28)=, provided that at least one of X21 to X23, and X26 to X28 represents —N═, R28 represents a hydrogen atom or a substituent, and when a plurality of —C(R28)= exists, the plurality of R28s may be the same or different, provided that at least one of R28s represents a substituent selected from the group consisting of a pyridyl group, a pyrimidinyl group, a pyradinyl group, a pyridazinyl group, and a triazinyl group; and

wherein R31 to R37 each represent a hydrogen atom or a substituent; X31 to X35 each represent —C(R38)=, or —N═, provided that at least one of X31 to X32 represents —N═, and R38 represents a hydrogen atom or a substituent, and at least one of X31 to X35 represents —C(R38)= in which R38 represents an aromatic heterocyclic group, and when a plurality of —C(R38)= exists, the plurality of R38s may be the same or different.

2. The organic electroluminescence element of claim 1 ,
wherein in Formula (2), R11 to R14, R16, and R17 each represent a hydrogen atom; and X11, X12 and X14 to X17 each represent —CH═.

3. The organic electroluminescence element of claim 1 ,
wherein X21, X22, X27 and X28 in Formula (3) each represent —CH═, or —N═.

4. The organic electroluminescence element of claim 1 ,
wherein R31 to R34, R36 and R37 in Formula (4) each represent a hydrogen atom; and X33 represents —CH═, or —N═.

5. The organic electroluminescence element of claim 1 ,
wherein the compound represented by any one of Formulas (2) to (4) contains as a partial structure at least one pyridine ring or one condensed aromatic heterocycle containing a pyridine ring.

6. The organic electroluminescence element of claim 1 ,
wherein the metal element is sodium, potassium or cesium.

7. The organic electroluminescence element of claim 1 ,
wherein the phosphorescence emitting organic metal complex is a compound represented by Formula (5):

wherein P and Q each represent a carbon atom or a nitrogen atom; A1 represents a group of atoms necessary to form an aromatic hydrocarbon ring or an aromatic heterocycle together with P—C; A2 represents a group of atoms necessary to form an aromatic heterocycle together with Q-N; P 1 -L1-P 2 represents a bidentate ligand, P 1 and P 2 each independently represent a carbon atom, a nitrogen atom, or an oxygen atom, and L1 represents a group of atoms necessary to form a bidentate ligand together with P 1 and P 2 ; j1 is an integer of 1 to 3, and j2 is an integer of 0 to 2, provided that the sum of j1 and j2 is 2 or 3; M 1 represents a metal element of Group 8 to Group 10 in the periodic table.

8. The organic electroluminescence element of claim 7 ,
wherein the compound represented by Formula (5) is a compound represented by Formula (6):

wherein Z represents a hydrocarbon ring group or a heterocyclic group; P and Q each represent a carbon atom or a nitrogen atom; A1 represents a group of atoms necessary to form an aromatic hydrocarbon ring or an aromatic heterocycle together with P—C; A3 represents —C(R 01 )═C(R 02 )—, —N═C(R 02 )—, —C(R 01 )=N—, or —N═N—, and R 01 and R 02 each represent a hydrogen atom or a substituent; P 1 -L1-P 2 represents a bidentate ligand, P 1 and P 2 each independently represent a carbon atom, a nitrogen atom, or an oxygen atom, and L1 represents a group of atoms necessary to form a bidentate ligand together with P 1 and P 2 ; j1 is an integer of 1 to 3, and j2 is an integer of 0 to 2, provided that the sum of j1 and j2 is 2 or 3; and M 1 represents a transition metal element of Group 8 to Group 10 in the periodic table.

9. The organic electroluminescence element of claim 8 ,
wherein the compound represented by Formula (6) is a compound represented by Formula (7):

wherein R 03 represents a substituent; R 04 represents a hydrogen atom or a substituent, and a plurality of R 04 s may be joined together to form a ring, n01 is an integer of 1 to 4; R 05 represents a hydrogen atom or a substituent, and a plurality of R 05 s may be joined together to form a ring, n02 is an integer of 1 to 2; R 06 represents a hydrogen atom or a substituent, and a plurality of R 06 s may be joined together to form a ring, n03 is an integer of 1 to 4; Z1 represents a group of atoms necessary to form a 6-membered aromatic hydrocarbon ring, or a 5 or 6-membered aromatic heterocycle together with C—C; Z2 represents a group of atoms necessary to form a hydrocarbon ring or a heterocycle; P 1 -L1-P 2 represents a bidentate ligand, P 1 and P 2 each independently represent a carbon atom, a nitrogen atom, or an oxygen atom, and L1 represents a group of atoms necessary to form a bidentate ligand together with P 1 and P 2 ; j1 is an integer of 1 to 3, and j2 is an integer of 0 to 2, provided that the sum of j1 and j2 is 2 or 3; M 1 represents a transition metal element of Group 8 to Group 10 in the periodic table; and R 03 and R 06 , R 04 and R 06 , and R 05 and R 06 may be joined together to form a ring.

10. The organic electroluminescence element of claim 9 ,
wherein the compound represented by Formula (7) is a compound represented by Formula (8):

wherein R 03 represents a substituent; R 04 represents a hydrogen atom or a substituent, and a plurality of R 04 s may be joined together to form a ring, n01 is an integer of 1 to 4; R 05 represents a hydrogen atom or a substituent, and a plurality of R 05 s may be joined together to form a ring, n02 is an integer of 1 to 2; R 06 represents a hydrogen atom or a substituent, and a plurality of R 06 s may be joined together to form a ring, n03 is an integer of 1 to 3; R 07 represents a substituent or a single bond; P 1 -L1-P 2 represents a bidentate ligand, P 1

Assignees

• Katakura Rie
• Katoh Eisaku
• Taka Hideo
• Konica Minolta Inc

Inventors

• Katakura Rie
• Katoh Eisaku
• Taka Hideo

Classifications

• H01L51/0072

  Electricity · mapped topic

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C09K2211/1466

  containing nitrogen as the only heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title