Organic electroluminescent element, method for producing organic electroluminescent element, display, and lighting device
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).
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), X 1 represents an oxygen atom or a sulfur atom; Z 2 , Z 3 , Z 5 to Z 8 independently represent ═N— or ═C(R 1 )— respectively; R 1 represents a hydrogen atom or a substituent; Z 4 is ═N—, Z 1 represents ═N— or ═C(R 2 )—, and R 2 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), W 1 represents —N— or ═C—; W 2 to W 5 independently represent ═N— or ═C(R 4 )— respectively; R 4 represents a hydrogen atom or a substituent; at least one of W 1 to W 5 represents ═N—; * represents a linkage position to the general formula (A5), and if two of ═C(R 4 )— are adjacently placed in series, two of R 4 may be condensed together to form a ring;
in the general formula (A5-5), Y 1 , Y 2 , and Y 5 to Y 9 independently represent ═N— or ═C(R 3 )— respectively; R 3 represents a hydrogen atom or a substituent; at least one of Y 1 , Y 2 and Y 5 represents ═N—; * represents a linkage position to the general formula (A5), X 2 represents one member selected from an oxygen atom, a sulfur atom, —NR 2 —, and —CR 3 R 4 —, wherein R 2 and R 4 are identical to said R 2 and R 4 , respectively;
in the general formula (A5-6), Y 1 , Y 2 and Y 5 to Y 9 independently represent ═N— or ═C(R 3 )— respectively; R 3 represents a hydrogen atom or a substituent; at least one of Y 1 , Y 2 and Y 5 represents ═N—; * represents a linkage position to the general formula (A5), X 2 represents one member selected from an oxygen atom, a sulfur atom, —NR 2 — or —CR 3 R 4 —, wherein R 2 and R 4 are identical to said R 2 and R 4 , respectively.
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), X 1 represents an oxygen atom or a sulfur atom; Z 2 , Z 3 , Z 5 to Z 8 independently represent ═N— or ═C(R 1 )— respectively; R 1 represents a hydrogen atom or a substituent; Z 4 is ═N—, Z 1 represents ═N— or ═C(R 2 )—, and R 2 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), W 1 represents —N— or ═C—; W 2 to W 5 independently represent ═N— or ═C(R 4 )— respectively; R 4 represents a hydrogen atom or a substituent; at least one of W 1 to W 5 represents ═N—; * represents a linkage position to the general formula (A5), and if two of ═C(R 4 )— are adjacently placed in series, two of R 4 may be condensed together to form a ring;
wherein in the general formula (A5-7), Y 1 to Y 3 , and Y 6 to Y 9 independently represent ═N— or ═C(R 3 )— respectively; R 3 represents a hydrogen atom or a substituent; at least one of Y 1 to Y 3 represents ═N—; * represents a linkage position to the general formula (A5), X 2 represents one member selected from an oxygen atom, a sulfur atom, —NR 2 — or —CR 3 R 4 , R 2 and R 4 are identical to said R 2 and R 4 , respectively;
wherein in the general formula (A5-8), Y 1 to Y 3 , and Y 6 to Y 9 independently represent ═N— or ═C(R 3 )— respectively; R 3 represents a hydrogen atom or a substituent; at least one of Y 1 to Y 3 represents ═N—; * represents a linkage position to the general formula (A5), X 2 represents one member selected from an oxygen atom, a sulfur atom, —NR 2 — or —CR 3 R 4 —, R 2 and R 4 are identical to said R 2 and R 4 , respectively.
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):
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), X 1 represents an oxygen atom or a sulfur atom; Z 1 to Z 8 independently represent ═N— or ═C(R 1 )— respectively; R 1 represents a hydrogen atom or a substituent; at least one of Z 1 to Z 4 represents ═N—, if Z 4 is ═N—, Z 1 represents ═N— or ═C(R 2 )—, and R 2 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 Z 4 is ═C(R 1 )—, at least Z 3 represents ═N—;
wherein in the formula (A5-1), Y 1 to Y 5 independently represent ═N— or ═C(R 3 )— respectively; R 3 represents a hydrogen atom or a substituent; at least one of Y 1 to Y 5 represents ═N—; * represents a linkage position to the general formula (A5), if two of ═C(R 3 )— are adjacently placed in series, two of R 3 may be condensed together to form a ring;
wherein in the formula (A5-2), W 1 represents —N— or ═C—; W 2 to W 5 independently represent ═N— or ═C(R 4 )— respectively; R 4 represents a hydrogen atom or a substituent; at least one of W 1 to W 5 represents ═N—; * represents a linkage position to the general formula (A5), if two of ═C(R 4 )— are adjacently placed in series, two of R 4 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).
5. A method for producing an organic electroluminescent element, wherein the organic electroluminescent element described in claim 1 is prepared by a wet process.
6. A display comprising the organic electroluminescent element described in claim 1 .
7. A lighting device comprising the organic electroluminescent element described in claim 1 .