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US RE49,237 E1Granted
Organic electroluminescence device and electronic device
AssigneeIdemitsu Kosan Co., Ltd.
InventorsKazuki Nishimura, Sayaka Mizutani
Life of this patent
Estimating the term…
Abstract
An organic electroluminescence device includes: a cathode; an anode; and an organic layer having one or more layers and provided between the anode and the cathode, in which the organic layer includes an emitting layer, and the emitting layer includes a first host material, a second host material and a phosphorescent dopant material. The first host material is a compound represented by a formula (1) below. The second host material is a compound represented by a formula (4) below.
Claims42
An organic electroluminescence device, comprising:
- a cathode;
- an anode;
- and
- an organic layer having one or more layers and provided between the anode and the cathode, wherein
- the organic layer comprises an emitting layer,
- the emitting layer comprises a first host material, a second host material, and a phosphorescent dopant material,
- the first host material is a compound represented by a formula (1) below, and
- the second host material is a compound represented by a formula (4) one of formulae (7) to (9) below,
- where:
- X1 to X3 each are a nitrogen atom or CR1 with a proviso that at least one of two or three of X1 to X3 is a are nitrogen atom atoms;
- R1 independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
- A is represented by a formula (2) below;
- and
- Ar11 and Ar12 are each independently represented by the formula (2), or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- wherein Ar11 and Ar12 are different, one of Ar11 and Ar12 in the first host material is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted by a heterocyclic group, and where:
- HAr1 is represented by a formula (3) below;
- m is 1 or 2;
- when m is 1, L1 is a single bond or a divalent linking group derived from one of benzene, biphenyl, terphenyl, naphthalene and phenanthrene;
- when m is 2, L1 is a trivalent linking group and HAr1 are the same or different;
- the linking group in L1 is a substituted or unsubstituted divalent or trivalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent or trivalent heterocyclic group having 5 to 30 ring atoms, or a divalent or trivalent multiple linking group provided by bonding two or three groups selected from the aromatic hydrocarbon group and the heterocyclic group;
- and
- in the multiple linking group, the aromatic hydrocarbon group and the heterocyclic group forming the multiple linking group are mutually the same or different and are optionally mutually bonded to form a ring,
- where:
- Z11 to and Z18 each independently represent a nitrogen atom, CR11;
- Z12 to Z17 each independently represent CR11 or a carbon atom to be bonded to L1 by a single bond;
- Y1 represents an oxygen atom, a sulfur atom, SiR12R13 or a silicon atom to be bonded to L1 by a single bond;
- one of the carbon atom at Z12 to Z17 Z11 to Z18 and R11 to R13 and the silicon atom at Y1 is bonded to L1;
- with a proviso that when Z11 is CR11, the carbon atom at R11 is not bonded to L1 and when Z18 is CR11, the carbon atom at R11 is not bonded to L1;
- R11, represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzisoxazolyl group, a substituted or unsubstituted benzisothiazolyl group, a substituted or unsubstituted benzoxadiazolyl group, a substituted or unsubstituted benzothiadiazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted piperidinyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted piperazinyl group, a substituted or unsubstituted morpholyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, or a substituted or unsubstituted phenoxazinyl group;
- R12 and R13 represent the same as R1 of the formula (1);
- a plurality of R11 are mutually the same or different;
- adjacent ones of R11 are optionally bonded to each other to form a ring;
- R12 and R13 are mutually the same or different;
- and R12 and R13 are optionally bonded to each other to form a ring,
- where:
- Y2 is represented by a formula (4-B) below;
- one of Z21 to Z28 is a carbon atom to be bonded to L211 in a formula (5) below, or a pair of adjacent ones of Z21 to Z28 are carbon atoms to be bonded to b and c in one of formulae (6-1) to (6-4) below to form a fused ring;
- Z21 to Z28 which are not bonded to L211, b and c are CR21;
- R21 represents the same as R1 of the formula (1);
- and a plurality of R21 are mutually the same or different,
- where:
- Ar210 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
- p is an integer of 1 to 3;
- when p is 2 or more, a plurality of Ar210 are mutually the same or different;
- L2 represents a single bond or a linking group;
- the linking group in L2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a polyvalent multiple linking group provided by bonding two or three groups selected from the aromatic hydrocarbon group and the heterocyclic group;
- and
- in the multiple linking group, the aromatic hydrocarbon group and the heterocyclic group forming the multiple linking group are mutually the same or different and are optionally mutually bonded to form a ring,
- where:
- L211 is a single bond or a linking group which is bonded to one of Z21 to Z28 in the formula (4);
- the linking group in L211 is a substituted or unsubstituted divalent or trivalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent or trivalent heterocyclic group having 5 to 30 ring atoms, or a divalent or trivalent multiple linking group provided by bonding two or three groups selected from the aromatic hydrocarbon group and the heterocyclic group;
- in the multiple linking group, the aromatic hydrocarbon group and the heterocyclic group forming the multiple linking group are mutually the same or different and are optionally mutually bonded to form a ring;
- R211, R212, R213, and R214 represent a hydrogen atom;
- s2 is 4 and t2 is 3;
- Ar211 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
- R211 and R212 represent the same as R1 of the formula (1);
- s is 3 and t is 4;
- and
- a plurality of R211 and R212 are mutually the same or different,
- where:
- b and c are bonded to one of the pair of adjacent ones of Z21 to Z28 to form a fused ring;
- Ar221 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
- R221 to R223 represent the same as R1 of the formula (1);
- u is 4;
- a plurality of R221 are mutually the same or different;
- and adjacent ones of R221 are optionally bonded to each other to form a ring.
63 more elements
An organic electroluminescence device, comprising:
- a cathode;
- an anode;
- and
- an organic layer having one or more layers and provided between the anode and the cathode, wherein
- the organic layer comprises an emitting layer,
- the emitting layer comprises a first host material, a second host material, and a phosphorescent dopant material,
- the first host material is a compound represented by a formula (1) below, and
- the second host material is a compound represented by a formula (30) below,
- where:
- X1 to X3 each are a nitrogen atom or CR1 with a proviso that at least one of X1 to X3 is a nitrogen atom;
- R1 independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
- A is represented by a formula (2) below;
- Ar11 and Ar12 are each independently represented by the formula (2), or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- (HAr1)mL1- (2)
- where:
- HAr1 is represented by a formula (3) below;
- m is 1 or 2;
- when m is 1, L1 is a single bond or a divalent linking group;
- when m is 2, L1 is a trivalent linking group and HAr1 are the same or different;
- the linking group in L1 is a substituted or unsubstituted divalent or trivalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent or trivalent heterocyclic group having 5 to 30 ring atoms, or a divalent or trivalent multiple linking group provided by bonding two or three groups selected from the aromatic hydrocarbon group and the heterocyclic group;
- and
- in the multiple linking group, the aromatic hydrocarbon group and the heterocyclic group forming the multiple linking group are mutually the same or different and are optionally mutually bonded to form a ring,
- where:
- Z11 to Z18 each independently represent a nitrogen atom, CR11 or a carbon atom to be bonded to L1 by a single bond;
- Y1 represents an oxygen atom, a sulfur atom, SiR12R13 or a silicon atom to be bonded to L1 by a single bond;
- one of the carbon atom at Z11 to Z18 and R11 to R13 and the silicon atom at Y1 is bonded to L1;
- R11, R12 and R13 represent the same as R1 of the formula (1);
- a plurality of R11 are mutually the same or different;
- adjacent ones of R11 are optionally bonded to each other to form a ring;
- R12 and R13 are mutually the same or different;
- and
- R12 and R13 are optionally bonded to each other to form a ring,
- where:
- Ar230 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms;
- Y3 is selected from an oxygen atom, a sulfur atom, NR230 and a nitrogen atom to be bonded to L3 by a single bond;
- L3 is a single bond or a linking group and the linking group is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms;
- L3 is optionally bonded to a carbon atom of the group including Y3, or is optionally bonded to Y3 when Y3 is a nitrogen atom;
- w is 1 or 2;
- when w is 1, two Ar230 are mutually the same or different;
- when w is 2, structures represented by a formula (30-1) below are mutually the same or different;
- R230 to R232 each independently represent the same as R1 of the formula (1);
- u3 and u4 are each independently an integer of 3 to 4;
- a plurality of R231 are mutually the same or different;
- adjacent ones of R231 are optionally bonded to each other to form a ring;
- R232 are mutually the same or different;
- and
- adjacent ones of R232 are optionally bonded to each other to form a ring,
- Y3, L3, R231, R232, u3 and u4 respectively represent the same as Y3, L3, R231, R232, u3 and u4 of the formula (30).
45 more elements
An organic electroluminescence device, comprising:
- a cathode;
- an anode;
- and
- an organic layer having one or more layers and provided between the anode and the cathode, wherein
- the organic layer comprises an emitting layer,
- the emitting layer comprises a first host material, a second host material, and a phosphorescent dopant material,
- wherein
- the first host material is represented by one of the following formulae H1 and H13;
- the second host material is represented by one of the following formulae H5, H6, H7 and H8;
6 more elements
Dependencies are inferred from the claim text.