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1. (WO2018124313) COMPOSÉS HÉTÉROCYCLIQUES CONTENANT DE L'AZOTE POUR DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES
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CLAIMS

1. A compound of formula (I)


wherein

Ai, A2 and A3 each independently represent 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,


R1 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 31 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

B is H, CN, 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 substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms;

L is a single bond, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms, a substituted silylene group having 2 to 30 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; and

I is 1 , 2 or 3, in the case that I is 2 or 3, L is the same or different in each occurrence.

2. The compound according to claim 1 , wherein

the compound of formula (I) is represented by formula (la)


wherein

Z2 is N or CR2; Z3 is N or CR3; Z4 is N or CR4; Z5 is N or CR5;

R2, R3, R4, and R5 each independently represent hydrogen, CN, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 31 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that,

two or more substituents selected from R2, R3, R4, and R5 may be bonded to each other to form a ring structure.

The compound according to claim 1 or 2, wherein

the compound of formula (I) is represented by formula (Ia1)


wherein

Z2 is N or CR2; Z3 is N or CR3; Z4 is N or CR4; Z5 is N or CR5, Z6 is N or CR6; Z7 is N or CR7; Z8 is N or CR8; Z9 is N or CR9; Z10 is N or CR10; Zn is N or CR11; Z12 is N or CR12; Z13 is N or CR13;

R2, R3, R4, R5 R6, R7, R8, R9, R10, R11, R12 and R13 each independently represent hydrogen, CN, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; a substituted or

unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; a substituted or

unsubstituted aralkyl group having 7 to 31 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 30 ring; provided that,

two or more substituents selected from R2, R3, R4, and R5, and/or two or more substituents selected from R6, R7, R8 and R9, and/or two or more substituents selected from R10, R11, R12 and R13 may be bonded to each other to form a ring structure.

4. The compound according to any one of claims 1 to 3, wherein the compound of formula (I) is represented by formula (laa


wherein

Z2 is N or CR2; Z3 is N or CR3; 2A is N or CR4; Z5 is N or CR5, Z6 is N or CR6; Z7 is N or CR7; Z8 is N or CR8; Z9 is N or CR9; Z10 is N or CR10; Zn is N or CR11; Z12 is N or CR12; Z13 is N or CR13;

R2, R3, R4, R5 R6, R7, R8, R9, R10, R11, R12 and R13 each independently represent hydrogen, CN, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; a substituted or

unsubstituted aralkyl group having 7 to 31 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 30 ring; provided that,

two or more substituents selected from R2, R3, R4, and R5, and/or two or more substituents selected from R6, R7, R8 and R9, and/or two or more substituents selected from R10, R11, R12 and R13 may be bonded to each other to form a ring structure.

5. The compound according to any one of claims 1 to 4, wherein

the compound of formula (I) is represented by formula (laaa)

wherein

R2, R3, R4, R5 R6, R7, R8, R9, R10, R11, R12 and R13 each independently represent hydrogen, CN a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; a substituted or

unsubstituted aralkyl group having 7 to 31 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 30 ring; provided that,

two or more substituents selected from R2, R3, R4, and R5, and/or two or more substituents selected from R6, R7, R8 and R9, and/or two or more substituents selected from R10, R11, R 2 and R13 may be bonded to each other to form a ring structure.

The compound according to any one of claims 1 to 5, wherein L is a single bond, 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; and

I is 1 or 2, in the case that I is 2, L is the same or different in each occurrence, B1 is H; CN; 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.

The compound according to any one of claims 1 to 6, wherein B1 represents general formula IX),


wherein

X1, X2 and X3 each independently represent CR23 or N, preferably at least one of X1, X2 and X3 is N;

R21, R22, R23 and R26 each independently represent hydrogen, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or

unsubstituted alkenyl group having 2 to 31 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, 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, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted silyl group having 3 to 60 carbon atoms, or a cyano group, preferably, R21, R22 R23 ancj R26 eacn independently represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, 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 cyano group, more preferably, R21, R22, R23 and R26 each independently represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group; a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, preferably phenyl group, 1 -naphthyl group, 2-naphthyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, phenanthrene-9-yl group, phenanthrene-3-yl group, phenanthrene-2-yl group, triphenylene-2-yl group, 9,9-dimethylfluorene-2-yl group, fluoranthene-3-yl group; a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, preferably triazine ring, pyrimidine ring, pyridine ring, dibenzofuran-2-yl group, dibenzofuran-4-yl group, 9-phenylcarbazole-3-yl group, 9-phenylcarbazole-2-yl group, dibenzothiophene-2-yl group, and dibenzothiophene-4-yl group; or a cyano group;

provided that, among R2 , R22, R26 and R23, if X1, X2 and/or X3 are CR23, any two of R2 , R22, R23 and R26 may be bonded each other to form a ring structure;

wherein one of R21, R22, R26 and, if X1, X2 and/or X3 are CR23, R23, represents a bonding site to -(L)i-.

8. The compound according to any one of claims 1 to 7, wherein L is selected from a

substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group.

The compound according to any one of claims 1 to 7, wherein L represents substituted unsubstituted aryl group having 6 to 30 carbon atoms, B1 represents CN.

10. A material for an organic electroluminescence device comprising at least one compound according to any one of claims 1 to 9.

11. An organic electroluminescence device which comprises an organic thin film layer between a cathode and an anode, wherein the organic thin film layer comprises one or more layers and comprises a light emitting layer, and at least one layer of the organic thin film layer comprises at least one compound according to any one of claims 1 to 9.

The organic electroluminescence device according to claim 11 , wherein the light emitting layer comprises at least one compound according to any one of claims 1 to 9.

13. The organic electroluminescence device according to claim 11 or claim 12, wherein the light emitting layer comprises a phosphorescent material, which is an ortho-metallated complex comprising a metal atom selected from iridium (Ir), osmium (Os) and platinum (Pt).

14. The organic electroluminescence device according to any one of claims 11 to 13, wherein an electron transporting layer is provided between the cathode and the light emitting layer, and the electron transporting layer comprises at least one compound according to any one of claims 1 to 9.

15. The organic electroluminescence device according to any one of claims 11 to 13, wherein a hole blocking layer is provided between the electron transporting layer and the light emitting layer, and the hole blocking layer comprises at least one compound according to any one of claims 1 to 9.

An electronic equipment comprising the organic electroluminescence device according to any one of claims 11 to 15.

17. A process for preparing the compound according to any one of claims 1 to 9, wherein Zi is N, comprising the following steps

Ai) Reaction of a diamine (II) with an isothiocyanate (III) followed by cyclization with a carbodiimide (IV), whereby a seven membered heterocycle (V) is formed,

wherein

Y2 and Y3 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 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; and

X is a halogen, preferably Br or I; and

Cyclization of the seven membered heterocycle (V) in the presence of a copper salt, whereb a heterocyclic system (VI) is formed


wherein

Ai, A2 and A3 each independently represent 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.

8. A process for preparing the compound according to any one of claims 1 to 9, wherein Zi is CR1, comprising the following step

Bi) Acid mediated ring closure of a compound of formula (VII) whereby a heterocyclic s stem of formula (VIII) is formed


wherein

Ai, A2 and A3 each independently represent 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, and

R1 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 31 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.