Aromatic amine derivative, and organic electroluminescent element using same

• US 10,014,477 B2
• Filed: 08/29/2013
• Issued: 07/03/2018
• Est. Priority Date: 08/31/2012
• Status: Active Grant

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Kato, Tomoki, Sado, Takayasu, Fujiyama, Takahiro
• Primary Examiner(s): Yamnitzky, Marie R
• Assistant Examiner(s): Dahlburg, Elizabeth M.
• Application Number:
  US14/424,656
• Publication Number:
  US 20150243891A1
• Time in Patent Office: 1,769 Days
• Field of Search: 257 40, 257E5105, 257E51026, 257E51032, 257E51052, 257 88, 257 89, 257 90, 257 91, 257 92, 257 93, 257 94, 257 95, 257 96, 257 97, 257 98, 257 99, 257100, 257101, 257102, 257103, 257E51001, 257E51002, 257E51003, 257E51004, 257E51005, 257E51006, 257E51007, 257E51008, 257E51009, 257E5101, 257E51011, 257E51012, 257E51013, 257E51014, 257E51015, 257E51016, 257E51017, 257E51018, 257E51019, 257E5102, 257E51021, 257E51022, 257E51023, 257E51024, 257E51025, 257E51027, 257E51028, 257E51029, 257E5103, 257E51031, 257E51033, 257E51034, 257E51035, 257E51036, 257E51037, 257E51038, 257E51039, 257E5104, 257E51041, 257E51042, 257E51043, 257E51044, 257E51045, 257E51046, 257E51047, 257E51048, 257E51049, 257E51051, 549 43, 549460, 564308, 428690, 428917, 428691, 313498, 313499, 313500, 313501, 313502, 313503, 313504-506, 313507, 313508, 313509, 313510, 313511, 313512, 528394, 528397, 528422, 5483041, 548418, 548440, 548444, 546 18, 546 79, 546 81, 546101, 544234, 427 58, 427 66, 25230116, 25230117, 25230118, 25230119, 2523012, 25230121, 25230122, 25230123, 25230124, 25230125, 25230126, 25230127, 25230128, 25230129, 2523013, 25230131, 25230132, 25230133, 25230134, 25230135
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 217/80 having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
• CPC Class Codes: C07C 217/92 the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 255/58 containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C09B 11/04 derived from triarylmethanes , i.e. central C-atom is substituted by amino, cyano, alkyl
• 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: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• 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 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 : containing sulfur as the only heteroatom
• 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 50/17 : Carrier injection layers
• CPC Class Codes: H10K 50/81 : Anodes
• CPC Class Codes: H10K 50/82 : Cathodes
• CPC Class Codes: H10K 85/615 : Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/626 : containing more than one polycyclic condensed aromatic rings, e.g. bis-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 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

An aromatic amine derivative represented by formula (1):

wherein R¹, R², R³, L, AR¹, Ar², k, m, and n are the same as defined in the specification, is useful as a material for an organic EL device and realizes an organic EL device with a high efficiency and a long lifetime even when driving it at a low voltage.

Claims

1. An organic electroluminescence device comprising an anode, a cathode, and at least one organic thin film layer disposed between the anode and the cathode, wherein:

the at least one organic thin film layer comprises a light emitting layer; and

at least one organic thin film layer comprises an aromatic amine derivative represented by formula (20);

2. The organic electroluminescence device according to claim 1, wherein the at least one organic thin film layer comprises a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer comprises the aromatic amine derivative.

3. The organic electroluminescence device according to claim 1, wherein Ar¹ represents a group represented by formula (30):

4. The organic electroluminescence device according to claim 3, wherein Ar² is represented by

5. The organic electroluminescence device according to claim 1, wherein a layer of the at least one organic thin film layer, which is closest to the light emitting layer, comprises the aromatic amine derivative.

6. The organic electroluminescence device according to claim 5, wherein the aromatic amine derivative is selected from the following compounds:

7. The organic electroluminescence device according to claim 5, wherein the aromatic amine derivative is

8. The organic electroluminescence device according to claim 1, wherein R² and R³ independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

9. The organic electroluminescence device according to claim 1, wherein each of R² and R³ is a hydrogen atom.

10. The organic electroluminescence device according to claim 1, wherein Ar² is represented by

11. The organic electroluminescence device according to claim 1, wherein each of R⁴ and R⁵ is a methyl group or a phenyl group.

12. The organic electroluminescence device according to claim 1, wherein the aromatic amine derivative is selected from the following compounds:

13. The organic electroluminescence device according to claim 1, wherein the aromatic amine derivative is