IP Library › Granted Patent US 12,369,490
Granted Patent B2
US 12,369,490 · App. 17/511,477 · Granted Jul 22, 2025

Organic electroluminescent element, organic electroluminescent display device, and electronic device

Inventors: Masato Nakamura (Sodegaura, JP); Yusuke Takahashi (Sodegaura, JP); Keitaro Yamada (Sodegaura, JP); Tasuku Haketa (Sodegaura, JP); Emiko Kambe (Sodegaura, JP); Kazuki Nishimura (Sodegaura, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H10K85/636H10K85/40H10K85/623H10K85/624H10K85/626H10K85/633H10K85/655H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K50/12H10K50/13H10K50/156H10K59/879H10K2101/10H10K2101/30H10K2101/40
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Quick Facts
Patent No.
US 12,369,490
App. No.
17/511,477
Granted
Jul 22, 2025
Kind
B2
Abstract

An organic electroluminescence device includes an emitting region provided between a cathode and an anode, a first anode side organic layer, a second anode side organic layer, and a third anode side organic layer, in which the emitting region includes at least one emitting layer, the second anode side organic layer contains at least one compound different from the compound contained in the third anode side organic layer, the third anode side organic layer has a film thickness of 20 nm or more, and a difference NM 2 −NM 3 between a refractive index NM 2 of a constituent material contained in the second anode side organic layer and a refractive index NM 3 of a constituent material contained in the third anode side organic layer satisfies a relationship of a numerical formula (Numerical Formula N1) below, NM 2 −NM 3 ≥0.05  (Numerical Formula N1).

Claims (213)

1. An organic electroluminescence device comprising:

a cathode;

an anode;

an emitting region provided between the cathode and the anode; and

a hole transporting zone provided between the anode and the emitting region, wherein

the emitting region comprises at least one emitting layer,

the at least one emitting layer in the emitting region comprises an emitting compound that emits light having a maximum peak wavelength of 500 nm or less or emits light having a maximum peak wavelength in a range from 500 nm to 550 nm, the at least one emitting layer in the emitting region does not comprise an iridium complex;

the hole transporting zone comprises at least a first anode side organic layer, a second anode side organic layer, and a third anode side organic layer,

the first anode side organic layer, the second anode side organic layer, and the third anode side organic layer are arranged between the anode and the emitting region in this order from the anode,

the first anode side organic layer comprises a first organic material and a second organic material,

the first organic material and the second organic material are different from each other,

a content of the second organic material in the first anode side organic layer is less than 50 mass %,

a constituent material comprised in the second anode side organic layer is at least one compound selected from the group consisting of a compound represented by a formula (C1) below and a compound represented by a formula (C3) below,

a constituent material comprised in the third anode side organic layer is a compound represented by the formula (C1),

the second anode side organic layer comprises at least one compound different from the compound comprised in the third anode side organic layer,

a difference NM 2 −NM 3 between a refractive index NM 2 at 460 nm of the constituent material comprised in the second anode side organic layer and a refractive index NM 3 at 460 nm of the constituent material comprised in the third anode side organic layer satisfies a relationship of a numerical formula (Numerical Formula N1) below, and

the third anode side organic layer has a film thickness of 20 nm or more,

NM 2 −NM 3 ≥0.05  (Numerical Formula N1)

where in the formula (C1):

L A1 , L A2 , and L A3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

Ar 111 , Ar 112 , and Ar 113 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R C1 )(R C2 )(R C3 );

R C1 , R C2 , and R C3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

when a plurality of R C1 are present, the plurality of R C1 are mutually the same or different;

when a plurality of R C2 are present, the plurality of R C2 are mutually the same or different; and

when a plurality of R C3 are present, the plurality of R C3 are mutually the same or different; and

the compound represented by the formula (C1) and comprised in the third anode side organic layer is a monoamine compound;

where in the formula (C3):

L C1 , L C2 , L C3 , and L C4 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

n2 is 1, 2, 3, or 4;

when n2 is 1, L C5 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

when n2 is 2, 3, or 4, a plurality of L C5 are mutually the same or different;

when n2 is 2, 3, or 4, a plurality of L C5 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

L C5 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

Ar 131 , Ar 132 , Ar 133 , and Ar 134 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R C1 )(R C2 )(R C3 );

R C1 , R C2 , and R C3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

when a plurality of R C1 are present, the plurality of R C1 are mutually the same or different;

when a plurality of R C2 are present, the plurality of R C2 are mutually the same or different; and,

when a plurality of R C3 are present, the plurality of R C3 are mutually the same or different; and,

in the compound represented by the formula (C1) and the compound represented by the formula (C3), a substituent for the “substituted or unsubstituted” group is not a group represented by —N(R C6 )(R C7 ), and R C6 and R C7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

wherein none of L A1 , L A2 , L A3 , Ar 111 , Ar 112 , and Ar 113 of the compound comprised in the second anode side organic layer and represented by the formula (C1) is 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group or 4-carbazolyl group,

none of L C1 , L C2 , L C3 , L C4 , L C5 , Ar 131 , Ar 132 , Ar 133 , and Ar 134 of the compound comprised in the second anode side organic layer and represented by the formula (C3) is 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group or 4-carbazolyl group, and

no substituent of the substituted or unsubstituted groups L A1 , L A2 , L A3 , Ar 111 , Ar 112 , Ar 113 , L C1 , L C2 , L C3 , L C4 , L C5 , Ar 131 , Ar 132 , Ar 133 , and Ar 134 in the compound comprised in the second anode side organic layer is 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group or 4-carbazolyl group.

2. The organic electroluminescence device according to claim 1 , wherein a first amino group represented by a formula (C3-1) below and a second amino group represented by a formula (C3-2) below in the compound represented by the formula (C3) are an identical group,

where in the formulae (C3-1) and (C3-2), * each represent a bonding position to L C5 .

3. The organic electroluminescence device according to claim 1 , wherein the third anode side organic layer has a film thickness in a range from 20 nm to 60 nm.

4. The organic electroluminescence device according to claim 1 , wherein the difference NM 2 −NM 3 between the refractive index NM 2 of the constituent material comprised in the second anode side organic layer and the refractive index NM 3 of the constituent material comprised in the third anode side organic layer satisfies a relationship of a numerical formula (Numerical Formula N3) below,

NM 2 −NM 3 ≥0.075  (Numerical Formula N3).

5. The organic electroluminescence device according to claim 1 , wherein the difference NM 2 −NM 3 between the refractive index NM 2 of the constituent material comprised in the second anode side organic layer and the refractive index NM 3 of the constituent material comprised in the third anode side organic layer satisfies a relationship of a numerical formula (Numerical Formula N2) below,

NM 2 −NM 3 ≥0.10  (Numerical Formula N2).

6. The organic electroluminescence device according to claim 1 , wherein the compound comprised in the second anode side organic layer comprises a plurality of compounds, and

all the compounds comprised in the second anode side organic layer are different from the compound comprised in the third anode side organic layer.

7. The organic electroluminescence device according to claim 1 , wherein the at least one compound selected from the group consisting of the compound represented by the formula (C1) and the compound represented by the formula (C3) has a refractive index of 1.94 or more.

8. The organic electroluminescence device according to claim 1 , wherein the compound comprised in the third anode side organic layer has a refractive index of 1.89 or less.

9. The organic electroluminescence device according to claim 1 , wherein the emitting region comprises a fluorescent substance and an organic compound.

10. The organic electroluminescence device according to claim 1 , wherein the emitting region comprises one emitting layer.

11. The organic electroluminescence device according to claim 1 , wherein the emitting region consists of one emitting layer.

12. The organic electroluminescence device according to claim 1 , wherein the emitting region consists of two emitting layers.

13. The organic electroluminescence device according to claim 1 , further comprising a fourth anode side organic layer, wherein

the fourth anode side organic layer is provided between the third anode side organic layer and the emitting region.

14. The organic electroluminescence device according to claim 13 , wherein a total of a film thickness of the first anode side organic layer, a film thickness of the second anode side organic layer, a film thickness of the third anode side organic layer, and a film thickness of a fourth anode side organic layer is 150 nm or less.

15. The organic electroluminescence device according to claim 1 , wherein the third anode side organic layer and the emitting region are in direct contact with each other.

16. The organic electroluminescence device according to claim 1 , wherein a ratio of a film thickness of the third anode side organic layer to a film thickness of the second anode side organic layer satisfies a relationship of a numerical formula (Numerical Formula A3) below,

0.75<TL 3 /TL 2 <3.0  (Numerical Formula A3)

where TL 2 is a film thickness of the second anode side organic layer, TL 3 is a film thickness of the third anode side organic layer, and a unit of the film thickness is denoted by nm.

17. The organic electroluminescence device according to claim 1 , wherein a total of a film thickness of the second anode side organic layer and a film thickness of the third anode side organic layer is 100 nm or more.

18. The organic electroluminescence device according to claim 1 , wherein a total of a film thickness of the first anode side organic layer, a film thickness of the second anode side organic layer, and a film thickness of the third anode side organic layer is 150 nm or less.

19. The organic electroluminescence device according to claim 1 , wherein

the third anode side organic layer comprises a third hole transporting zone material, which is the compound represented by the formula (C1),

a hole mobility of the third hole transporting zone material μh(cHT3) is larger than 1.0×10 −5 cm 2 /Vs, and

an energy level of a highest occupied molecular orbital of the third hole transporting zone material HOMO(cHT3) is −5.6 eV or less.

20. The organic electroluminescence device according to claim 1 , wherein

the second anode side organic layer comprises a second hole transporting zone material, which is the at least one compound selected from the group consisting of the compound represented by the formula (C1) and the compound represented by the formula (C3),

the third anode side organic layer comprises a third hole transporting zone material, which is the compound represented by the formula (C1),

the second hole transporting zone material and the third hole transporting zone material are different compounds,

a hole mobility of the second hole transporting zone material h(cHT2) is larger than 1.0×10 −4 cm 2 /Vs,

a hole mobility of the third hole transporting zone material h(cHT3) is larger than 1.0×10 −5 cm 2 /Vs, and

an energy level of a highest occupied molecular orbital of the second hole transporting zone material HOMO(cHT2) and an energy level of a highest occupied molecular orbital of the third hole transporting zone material HOMO(cHT3) satisfy a relationship of a numerical formula (Numerical Formula B1) below,

HOMO(cHT2)<HOMO(cHT3)  (Numerical Formula B1).

21. The organic electroluminescence device according to claim 1 , wherein

the third anode side organic layer comprises a third hole transporting zone material, which is the compound represented by the formula (C1), and

a singlet energy of the third hole transporting zone material is larger than 3.12 eV.

22. The organic electroluminescence device according to claim 1 , wherein the third anode side organic layer comprises at least one compound selected from the group consisting of a compound represented by a formula (cHT3-11), a compound represented by a formula (cHT3-2), a compound represented by a formula (cHT3-31), and a compound represented by a formula (cHT3-4) below,

where in the formulae (cHT3-11), (cHT3-2), (cHT3-31), and (cHT3-4):

Ar 311 is a group represented by one of a formula (1-a), a formula (1-b), a formula (1-c), and a formula (1-d) below;

Ar 312 and Ar 313 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R C1 )(R C2 )(R C3 );

R C1 , R C2 , and R C3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

when a plurality of R C1 are present, the plurality of R C1 are mutually the same or different;

when a plurality of R C2 are present, the plurality of R C2 are mutually the same or different;

when a plurality of R C3 are present, the plurality of R C3 are mutually the same or different;

L D1 , L D2 , and L D3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

one of R D26 to R D29 is a single bond with L D1 , and *k represents a bonding position;

at least one combination of adjacent two or more of R D21 to R D24 and R D26 to R D29 not being the single bond with L D1 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

at least one combination of adjacent two or more of R D31 to R D38 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

one of R D47 to R D50 is a single bond with L D1 , and *m represents a bonding position,

at least one combination of adjacent two or more of R D41 to R D44 and R D47 to R D50 not being the single bond with L D1 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

X 3 is an oxygen atom, a sulfur atom, or C(R D45 )(R D46 );

a combination of R D45 and R D46 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

R D25 , and R D21 to R D24 , R D26 to R D29 , R D31 to R D38 , and R D41 to R D50 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

in the compounds represented by the formulae (cHT3-11), (cHT3-2), (cHT3-31), and (cHT3-4), R 901 to R 904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;

when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;

when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different; and

when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different;

where in the formula (1-a):

none of a combination of adjacent two or more of R 51 to R 55 are bonded to each other;

R 51 to R 55 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and

** represents a bonding position to L D1 ,

where in the formula (1-b):

one of R 61 to R 68 is a single bond with *b;

none of a combination of adjacent two or more of R 61 to R 68 not being the single bond with *b are bonded to each other;

R 61 to R 68 not being the single bond with *b are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; and

** represents a bonding position to L D1 ,

where in the formula (1-c):

one of R 71 to R 80 is a single bond with *d;

none of a combination of adjacent two or more of R 71 to R 80 not being the single bond with *d are bonded to each other;

R 71 to R 80 not being the single bond with *d are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; and

** represents a bonding position to L D1 ,

where in the formula (1-d):

one of R 141 to R 145 is a single bond with *h1, and another one of R 141 to R 145 is a single bond with *h2;

none of a combination of adjacent two or more of R 141 to R 145 not being the single bond with *h1 and not being the single bond with *h2 are bonded to each other;

at least one combination of adjacent two or more of R 151 to R 155 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

at least one combination of adjacent two or more of R 161 to R 165 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

R 141 to R 145 not being the single bond with *h1 and not being the single bond with *h2 as well as R 151 to R 155 and R 161 to R 165 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; and

** represents a bonding position to L D1 .

23. The organic electroluminescence device according to claim 1 , wherein the second anode side organic layer comprises at least one compound selected from the group consisting of a compound represented by a formula (cHT2-2) and a compound represented by a formula (cHT2-3) below,

wherein the formulae (cHT2-2) and (cHT2-3):

Ar 12 , Ar 113 , Ar 121 , Ar 122 , Ar 123 , and Ar 24 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R C1 )(R C2 )(R C3 );

R C1 , R C2 , and R C3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

when a plurality of R C1 are present, the plurality of R C1 are mutually the same or different;

when a plurality of R C2 are present, the plurality of R C2 are mutually the same or different;

when a plurality of R C3 are present, the plurality of R C3 are mutually the same or different;

L A1 , L A2 , L A3 , L B1 , L B2 , L B3 , and L B4 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

nb is 1, 2, 3, or 4;

when nb is 1, L B5 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

when nb is 2, 3, or 4, a plurality of L B5 are mutually the same or different;

when nb is 2, 3, or 4, a plurality of L B5 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

L B5 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

a combination of R A35 and R A36 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

R A35 and R A36 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

at least one combination of adjacent two or more of R A30 to R A34 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

R A30 to R A34 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

in the compounds represented by the formulae (cHT2-2) and (cHT2-3), R 901 to R 904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;

when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;

when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different; and

when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different.

24. The organic electroluminescence device according to claim 22 , wherein the second anode side organic layer comprises at least one compound selected from the group consisting of a compound represented by a formula (cHT2-2) and a compound represented by a formula (cHT2-3) below,

where in the formulae (cHT2-2) and (cHT2-3):

Ar 112 , Ar 113 , Ar 121 , Ar 122 , Ar 123 , and Ar 124 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R C1 )(R C2 )(R C3 );

R C1 , R C2 , and R C3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

when a plurality of R C1 are present, the plurality of R C1 are mutually the same or different;

when a plurality of R C2 are present, the plurality of R C2 are mutually the same or different;

when a plurality of R C3 are present, the plurality of R C3 are mutually the same or different;

L A1 , L A2 , L A3 , L B1 , L B2 , L B3 , and L B4 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

nb is 1, 2, 3, or 4;

when nb is 1, L B5 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

when nb is 2, 3, or 4, a plurality of L B5 are mutually the same or different;

when nb is 2, 3, or 4, a plurality of L B5 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

L B5 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

a combination of R A35 and R A36 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

R A35 and R A36 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

at least one combination of adjacent two or more of R A30 to R A34 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

R A30 to R A34 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

in the compounds represented by the formulae (cHT2-2) and (cHT2-3), R 901 to R 904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;

when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;

when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different; and

when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different.

25. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (C1) is a monoamine compound.

26. The organic electroluminescence device according to claim 1 , further comprising:

two or more emitting units; and

at least one charge generating layer disposed between the two or more emitting units, wherein

at least one of the two or more emitting units is a first emitting unit comprising the hole transporting zone as a first hole transporting zone and the emitting region as a first emitting region.

27. An organic electroluminescence display device, comprising: an anode and a cathode arranged to face each other;

a blue-emitting organic EL device as a blue pixel;

a green-emitting organic EL device as a green pixel; and

a red-emitting organic EL device as a red pixel, wherein

the blue pixel comprises the organic electroluminescence device according to claim 1 as the blue-emitting organic EL device,

the green-emitting organic EL device comprises a green emitting region provided between the anode and the cathode,

the red-emitting organic EL device comprises a red emitting region provided between the anode and the cathode, and

the first anode side organic layer, the second anode side organic layer, and the third anode side organic layer are provided between the anode and the emitting region of the blue-emitting organic EL device, the green emitting region, and the red emitting region in a shared manner across the blue-emitting organic EL device, the green-emitting organic EL device, and the red-emitting organic EL device.

28. An organic electroluminescence display device, comprising:

an anode and a cathode arranged to face each other;

a blue-emitting organic EL device as a blue pixel;

a green-emitting organic EL device as a green pixel; and

a red-emitting organic EL device as a red pixel, wherein

the blue pixel, the green pixel, and the red pixel respectively comprise, as the blue-emitting organic EL device, the green-emitting organic EL device, and the red-emitting organic EL device, the organic electroluminescence device according to claim 1 ,

the emitting region in the blue-emitting organic EL device is a blue emitting region provided between the anode and the cathode,

the emitting region in the green-emitting organic EL device is a green emitting region provided between the anode and the cathode,

the emitting region in the red-emitting organic EL device is a red emitting region provided between the anode and the cathode, and

the first anode side organic layer, the second anode side organic layer, and the third anode side organic layer are provided between the anode and the blue emitting region, the green emitting region, and the red emitting region in a shared manner across the blue-emitting organic EL device, the green-emitting organic EL device, and the red-emitting organic EL device.

29. An electronic device comprising the organic electroluminescence device according to claim 1 .

30. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (C1) and comprised in the third anode side organic layer comprises a group represented by a formula (2-e) below, the group represented by the formula (2-e) being bonded directly, with a phenylene group, or with a biphenylene group to a nitrogen atom of an amino group of the monoamine compound;

where in the formula (2-e):

Z 3 is an oxygen atom, a sulfur atom, NR 319 , or C(R 320 )(R 321 );

one of R 311 to R 321 is a single bond with *e, or one of carbon atoms of a substituted or unsubstituted benzene ring, described below, formed by mutually bonding a combination of adjacent two or more of R 311 to R 318 is bonded to *e by a single bond;

a combination of adjacent two or more of R 311 to R 318 not being the single bond with *e are mutually bonded to form a substituted or unsubstituted benzene ring, or not mutually bonded;

R 311 to R 318 not being the single bond with *e and not forming the substituted or unsubstituted benzene ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 10 ring atoms;

R 319 not being the single bond with *e is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms;

a combination of R 320 and R 321 not being the single bond with *e are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;

R 320 and R 321 not being the single bond with *e, not forming the substituted or unsubstituted monocyclic ring, and not forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; and

** represents a bonding position.

31. The organic electroluminescence device according to claim 1 , wherein the emitting region does not comprise a heavy metal complex.

32. The organic electroluminescence device according to claim 1 , wherein the at least one emitting layer in the emitting region further comprises a second compound, wherein the second compound is represented by a formula (2) below:

wherein in the formula (2), R 201 to R 208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a group represented by —S—(R 905 ), a group represented by —N(R 906 )(R 907 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R 801 , a group represented by —COOR 802 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

L 201 and L 202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and

Ar 201 and Ar 202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

33. The organic electroluminescence device according to claim 32 , wherein a thickness of the third anode side organic layer is in a range from 20 nm to 75 nm.

34. The organic electroluminescence device according to claim 1 , wherein the first anode side organic layer comprises a compound represented by the formula (C1) as the first organic material,

no substituent of the substituted or unsubstituted groups L A1 , L A2 , L A3 , Ar 111 , Ar 112 , and Ar 113 in the compound comprised in the first anode side organic layer is 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group or 4-carbazolyl group,

no substituent for the substituted or unsubstituted group as to the compound comprised in the first anode side organic layer is 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group or 4-carbazolyl group,

none of L A1 , L A2 , L A3 , Ar 111 , Ar 112 , and Ar 113 of the compound comprised in the third anode side organic layer and represented by the formula (C1) is 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group or 4-carbazolyl group, and

no substituent of the substituted or unsubstituted groups L A1 , L A2 , L A3 , Ar 111 , Ar 112 , and Ar 113 in the compound comprised in the third anode side organic layer is 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group or 4-carbazolyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2021
From: NAKAMURA, MASATO; TAKAHASHI, YUSUKE; YAMADA, KEITARO; HAKETA, TASUKU; KAMBE, EMIKO; NISHIMURA, KAZUKI
To: IDEMITSU KOSAN CO.,LTD.
Reel/Frame 057921/0637 →
Priority Claims (5)
JP 2021-003672 · Jan 13, 2021 · national
JP 2021-023381 · Feb 17, 2021 · national
JP 2021-076715 · Apr 28, 2021 · national
JP 2021-096578 · Jun 9, 2021 · national
JP 2021-106128 · Jun 25, 2021 · national
Continuity (1)
Related Publication 20220231231A1 · Jul 21, 2022
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