# US 10,483,471 B2 · Organic electroluminescent element, method for producing organic electroluminescent element, display, and lighting device

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- Number: US 10,483,471 B2
- Document ID: US10483471B2
- Status: Granted
- Kind: B2
- Application number: 15/400,279
- Filed: 2017-01-06
- Published: 2017-07-06
- Granted: 2019-11-19
- Earliest claimed: 2016-01-06
- Assignees: Konica Minolta, Inc.
- Applicants: Konica Minolta, Inc.
- Inventors: Keiko Ishidai; Shinya Otsu; Noboru Sekine
- Web page: https://patentgrep.com/patent/US10483471B2

## CPC

- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C07D 403/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 85/342: {comprising iridium}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/16: Electron transporting layers
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Provided are an organic electroluminescent (EL) element having high luminescent efficiency, a small aging change in luminescent intensity even after the organic EL element is stored at a high temperature together with a long luminescent lifetime at a high temperature, and a method for producing the organic EL element. Further, a display and a lighting device including the organic EL element are also provided. The organic EL element contains an organic layer provided between at least a pair of a cathode and an anode. The organic layer is formed of at least one layer including a luminescent layer, and at least one layer forming the organic layer contains at least one of the compounds represented by the general formulae (A1) to (A5).

## Claims

### Claim 1

An organic electroluminescent element including an organic layer provided between at least a pair of a cathode and an anode, wherein
the organic layer is formed of at least one layer including a luminescent layer, and
at least one layer forming the organic layer contains at least one selected from compounds represented by general formulae (A2) and (A5):
wherein in the general formula (A2), X represents an oxygen atom or a sulfur atom;
wherein in the general formula (A5), X1 represents an oxygen atom or a sulfur atom; Z2, Z3, Z5 to Z8 independently represent ═N— or ═C(R1)— respectively; R1 represents a hydrogen atom or a substituent; Z4 is ═N—, Z1 represents ═N— or ═C(R2)—, and R2 represents a nitrogen-containing 6 membered heterocycle of general formula (A5-5) or (A5-6) or a nitrogen-containing 5 membered ring of general formula (A5-2);
in the formula (A5-2), W1 represents —N— or ═C—; W2 to W5 independently represent ═N— or ═C(R4)— respectively; R4 represents a hydrogen atom or a substituent; at least one of W1 to W5 represents ═N—; * represents a linkage position to the general formula (A5), and if two of ═C(R4)— are adjacently placed in series, two of R4 may be condensed together to form a ring;
in the general formula (A5-5), Y1, Y2, and Y5 to Y9 independently represent ═N— or ═C(R3)— respectively; R3 represents a hydrogen atom or a substituent; at least one of Y1, Y2 and Y5 represents ═N—; * represents a linkage position to the general formula (A5), X2 represents one member selected from an oxygen atom, a sulfur atom, —NR2—, and —CR3R4—, wherein R2 and R4 are identical to said R2 and R4, respectively;
in the general formula (A5-6), Y1, Y2 and Y5 to Y9 independently represent ═N— or ═C(R3)— respectively; R3 represents a hydrogen atom or a substituent; at least one of Y1, Y2 and Y5 represents ═N—; * represents a linkage position to the general formula (A5), X2 represents one member selected from an oxygen atom, a sulfur atom, —NR2— or —CR3R4—, wherein R2 and R4 are identical to said R2 and R4, respectively.

### Claim 2

An organic electroluminescent element including an organic layer provided between at least a pair of a cathode and an anode, wherein
the organic layer is formed of at least one layer including a luminescent layer, and
at least one layer forming the organic layer contains at least one selected from compounds represented by general formulae (A2) and (A5):
wherein in the general formula (A2), X represents an oxygen atom or a sulfur atom;
wherein in the general formula (A5), X1 represents an oxygen atom or a sulfur atom; Z2, Z3, Z5 to Z8 independently represent ═N— or ═C(R1)— respectively; R1 represents a hydrogen atom or a substituent; Z4 is ═N—, Z1 represents ═N— or ═C(R2)—, and R2 represents a nitrogen-containing 6 membered heterocycle of general formula (A5-7) or (A5-8) or a nitrogen-containing 5 membered ring of general formula (A5-2);
in the formula (A5-2), W1 represents —N— or ═C—; W2 to W5 independently represent ═N— or ═C(R4)— respectively; R4 represents a hydrogen atom or a substituent; at least one of W1 to W5 represents ═N—; * represents a linkage position to the general formula (A5), and if two of ═C(R4)— are adjacently placed in series, two of R4 may be condensed together to form a ring;
wherein in the general formula (A5-7), Y1 to Y3, and Y6 to Y9 independently represent ═N— or ═C(R3)— respectively; R3 represents a hydrogen atom or a substituent; at least one of Y1 to Y3 represents ═N—; * represents a linkage position to the general formula (A5), X2 represents one member selected from an oxygen atom, a sulfur atom, —NR2— or —CR3R4, R2 and R4 are identical to said R2 and R4, respectively;
wherein in the general formula (A5-8), Y1 to Y3, and Y6 to Y9 independently represent ═N— or ═C(R3)— respectively; R3 represents a hydrogen atom or a substituent; at least one of Y1 to Y3 represents ═N—; * represents a linkage position to the general formula (A5), X2 represents one member selected from an oxygen atom, a sulfur atom, —NR2— or —CR3R4—, R2 and R4 are identical to said R2 and R4, respectively.

### Claim 3

An organic electroluminescent element including an organic layer provided between at least a pair of a cathode and an anode, wherein
the organic layer is formed of at least one layer including a luminescent layer, and at least one layer forming the organic layer contains at least one selected from
compounds (4) to (6) and (11) to (14):

### Claim 4

An organic electroluminescent element including an organic layer provided between at least a pair of a cathode and an anode, wherein
the organic layer is formed of at least one layer including a luminescent layer, and
at least one layer forming the organic layer contains at least one selected from compounds represented by general formulae (A1) to (A5):
wherein in the general formulae (A1) to (A3), X represents an oxygen atom or a sulfur atom;
wherein in the general formula (A5), X1 represents an oxygen atom or a sulfur atom; Z1 to Z8 independently represent ═N— or ═C(R1)— respectively; R1 represents a hydrogen atom or a substituent; at least one of Z1 to Z4 represents ═N—, if Z4 is ═N—, Z1 represents ═N— or ═C(R2)—, and R2 represents a nitrogen-containing 6 membered heterocycle of general formula (A5-1) or a nitrogen-containing 5 membered ring of general formula (A5-2), if Z4 is ═C(R1)—, at least Z3 represents ═N—;
wherein in the formula (A5-1), Y1 to Y5 independently represent ═N— or ═C(R3)— respectively; R3 represents a hydrogen atom or a substituent; at least one of Y1 to Y5 represents ═N—; * represents a linkage position to the general formula (A5), if two of ═C(R3)— are adjacently placed in series, two of R3 may be condensed together to form a ring;
wherein in the formula (A5-2), W1 represents —N— or ═C—; W2 to W5 independently represent ═N— or ═C(R4)— respectively; R4 represents a hydrogen atom or a substituent; at least one of W1 to W5 represents ═N—; * represents a linkage position to the general formula (A5), if two of ═C(R4)— are adjacently placed in series, two of R4 may be condensed together to form a ring;
wherein
the luminescent layer includes an electron transfer layer, and
the electron transfer layer contains at least one of the compounds represented by the general formulae (A1) to (A5).

### Claim 5 (depends on 1)

A method for producing an organic electroluminescent element, wherein the organic electroluminescent element described in claim 1 is prepared by a wet process.

### Claim 6 (depends on 1)

A display comprising the organic electroluminescent element described in claim 1.

### Claim 7 (depends on 1)

A lighting device comprising the organic electroluminescent element described in claim 1.