COMPOUND, ORGANIC ELECTROLUMINESCENCE ELEMENT MATERIAL, INK COMPOSITION, ORGANIC ELECTROLUMINESCENCE ELEMENT, ELECTRONIC DEVICE, AND METHOD FOR PRODUCING COMPOUND

• US 20160197288A1
• Filed: 12/17/2014
• Published: 07/07/2016
• Est. Priority Date: 12/18/2013
• Status: Active Grant

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: IKEDA, Kiyoshi, KAWAKAMI, Hironori
• Granted Patent: US 10,032,991 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/008 Triarylamine dyes containing no other chromophores
• CPC Class Codes: C09B 69/109 containing other specific dyes
• CPC Class Codes: C09D 11/037 characterised by the pigment
• CPC Class Codes: C09D 11/50 Sympathetic, colour changing or similar inks
• CPC Class Codes: C09D 11/52 Electrically conductive inks
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 30/865 : Intermediate layers comprising a mixture of materials of the adjoining active layers
• CPC Class Codes: H10K 50/11 : characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 : Hole transporting layers
• CPC Class Codes: H10K 50/16 : Electron transporting layers
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/615 : Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/633 : comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

A compound represented by formula (1):

wherein *a, *b, R¹, X¹, L¹, L², n, A¹, and A² are as defined in the description, and a production method of the compound represented by formula (1) are provide. In the production method, A¹ is introduced under a reaction condition in which the reactivity of Hal² in a compound represented by formula (I):

wherein *c, *d, R¹, X¹, L¹, L², n, A¹, A², Hal¹, and Hal² are as defined in the description,
is extremely low as compared with that of Hal¹ and then A² which is different from A¹ is introduced under a reaction condition in which the reactivity of Hal² is high. The compound represented by formula (1) is formed into a layer by a coating method and meets various performance requirements of an organic EL device.

Claims

1. A compound represented by formula (1):

2. The compound according to claim 1, wherein

when *b is bonded to the carbon atom *c1, L¹ represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a group of atoms which completes a ring together with R²;

when L¹ represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and n is 1, L¹ and L² may be the same or different and may be crosslinked together, and

when L¹ represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and n is 2 or 3, L¹ and two or three groups L² may be the same or different, and L¹ and L², and two groups L² may be crosslinked together.

3. The compound according to claim 1, wherein

when *b is bonded to the carbon atom *c2 and n is 1, L¹ and L² may be the same or different and may be crosslinked together;

and

when *b is bonded to the carbon atom *c2 and n is 2 or 3, L¹ and two or three groups L² may be the same or different, and L¹ and L², and two groups L² may be crosslinked together.

4. The compound according to claim 1, wherein the compound is represented by formula (1a):

5. The compound according to claim 1, wherein the compound is represented by formula (1b):

6. The compound according to claim 1, wherein the compound is represented by formula (1c):

7. The compound according to claim 1, wherein A¹ and A² each represent a group represented by any of the following formulae:

8. The compound according to claim 1, wherein A¹ and A² each represent a group represented by any of the following formulae:

9. The compound according to claim 1, wherein the substituent represented by R¹ is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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 60 ring carbon atoms, an aralkyl group having 7 to 51 carbon atoms which includes an aryl group having 6 to 60 ring carbon atoms, an amino group, a mono- or di-substituted amino group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 ring carbon atoms, a silyl group, a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, and a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms.

10. The compound according to claim 1, wherein the substituent represented by R^a is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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 60 ring carbon atoms, an aralkyl group having 7 to 51 carbon atoms which includes an aryl group having 6 to 60 ring carbon atoms, an amino group, a mono- or di-substituted amino group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 ring carbon atoms, a silyl group, a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, and a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms.

11. The compound according to claim 1, wherein the substituent represented by any of R², R³, R⁹, and R¹⁰ is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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 60 ring carbon atoms, an aralkyl group having 7 to 51 carbon atoms which includes an aryl group having 6 to 60 ring carbon atoms, an amino group, a mono- or di-substituted amino group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 ring carbon atoms, a silyl group, a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, and a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms.

12. The compound according to claim 1, wherein the substituent represented by any of R⁴ to R⁸ and R¹¹ to R¹⁵ is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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 60 ring carbon atoms, an aralkyl group having 7 to 51 carbon atoms which includes an aryl group having 6 to 60 ring carbon atoms, an amino group, a mono- or di-substituted amino group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 ring carbon atoms, a silyl group, a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, and a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms.

13. The compound according to claim 1, wherein L¹ represents a m-phenylene group or a p-phenylene group.

14. The compound according to claim 2, wherein the ring formed when L¹ and R² are bonded to each other is selected from the group consisting of a fused or non-fused aromatic ring having 6 to 50 ring carbon atoms, a partially hydrogenated fused or non-fused aromatic ring having 6 to 50 ring carbon atoms, a fused or non-fused aromatic heterocyclic ring having 5 to 50 ring atoms, and a partially hydrogenated fused or non-fused aromatic heterocyclic ring having 5 to 50 ring atoms.

15. The compound according to claim 1, wherein the ring formed when R² and R¹ are bonded to each other is selected from the group consisting of a fused or non-fused aromatic ring having 6 to 50 ring carbon atoms, a partially hydrogenated fused or non-fused aromatic ring having 6 to 50 ring carbon atoms, a fused or non-fused aromatic heterocyclic ring having 5 to 50 ring atoms, and a partially hydrogenated fused or non-fused aromatic heterocyclic ring having 5 to 50 ring atoms.

16. The compound according to claim 1, wherein the ring formed when adjacent two groups R^a are bonded to each other is selected from the group consisting of a fused or non-fused aromatic ring having 6 to 50 ring carbon atoms, a partially hydrogenated fused or non-fused aromatic ring having 6 to 50 ring carbon atoms, a fused or non-fused aromatic heterocyclic ring having 5 to 50 ring atoms, and a partially hydrogenated fused or non-fused aromatic heterocyclic ring having 5 to 50 ring atoms.

17. The compound according to claim 1, wherein X^a to X^d each represent CR^a wherein R^a represents a hydrogen atom.

18. A material comprising the compound according to claim 1.

19. An ink composition comprising a solvent and the compound according to claim 1.

20. An organic electroluminescence device which comprises a cathode, an anode, and at least one organic thin film layer which is disposed between the cathode and the anode, wherein the at least one organic thin film layer comprises a light emitting layer and at least one layer of the at least one organic thin film layer comprises the compound according to claim 1.

21. The organic electroluminescence device according to claim 20, wherein the light emitting layer comprises the compound as a host material.

22. The organic electroluminescence device according to claim 20, wherein the light emitting layer comprises a phosphorescent emitting material.

23. The organic electroluminescence device according to claim 22, wherein the phosphorescent emitting material is an ortho-metallated complex of a metal selected from the group consisting of iridium (Ir), osmium (Os) and platinum (Pt).

24. The organic electroluminescence device according to claim 20, wherein the organic electroluminescence device comprises an electron transporting layer between the cathode and the light emitting layer and the electron transporting layer comprises the compound.

25. The organic electroluminescence device according to claim 20, wherein the organic electroluminescence device comprises a hole transporting layer between the anode and the light emitting layer and the hole transporting layer comprises the compound.

26. The organic electroluminescence device according to claim 20, wherein an interfacial region between the cathode and the organic thin film layer comprises an electron-donating dopant.

27. An electronic equipment comprising the organic electroluminescence device according to claim 20.

28. A method of producing the compound according to claim 1, which comprises a coupling reaction 1 and a coupling reaction 2:

(1) the coupling reaction 1, wherein a compound represented by formula (I);

29. The method according to claim 28, wherein the basic catalyst is at least one selected from the group consisting of an alkali metal carbonate, an alkali metal hydrogencarbonate, an alkaline earth metal carbonate, a metal phosphate, an alkali metal hydride, and a metal amide.

30. The method according to claim 28, wherein the transition metal catalyst comprises at least one transition metal selected from the group consisting of palladium, copper, platinum, rhodium, ruthenium, nickel, and iron.

31. The method according to any claim 28, wherein the base is at least one selected from the group consisting of an alkoxide, a carbonate salt, and a phosphate salt.