Organic electroluminescent compound and organic electroluminescent device comprising the same

• US 10,636,980 B2
• Filed: 07/27/2017
• Issued: 04/28/2020
• Est. Priority Date: 07/27/2016
• Status: Active Grant

• Current Assignee: Rohm and Haas Electronic Materials Korea, Ltd. (DuPont de Nemours, Inc.)
• Original Assignee: Rohm and Haas Electronic Materials Korea, Ltd. (DuPont de Nemours, Inc.)
• Inventors: Moon, Doo-Hyeon, Jun, Ji-Song
• Primary Examiner(s): Coleman, Brenda L
• Application Number:
  US16/315,178
• Publication Number:
  US 20190312212A1
• Time in Patent Office: 1,006 Days
• CPC Class Codes: C07D 487/16 Peri-condensed systems
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1018 Heterocyclic compounds
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/90 Multiple hosts in the emissive layer
• 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 85/342 comprising iridium
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• 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

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having low driving voltage, high luminous efficiency, and or excellent lifespan characteristic can be produced.

Claims

1. An organic electroluminescent compound represented by the following formula 1:

2. The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted (C1-C30)alkyl(ene), the substituted (C6-C30)aryl(ene), the substituted 3- to 30-membered heteroaryl(ene), the substituted (C3-C30)cycloalkyl(ene), the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di- (C1-C30)alkylamino, the substituted mono- or di- (C6-C30)arylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino in Ar, L, and R₁, and the substituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring in R₁ each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-30)alkyl, a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (C3-C30)cycloalkenyl, a 3- to 7-membered heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a 5- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a 5- to 30-membered heteroaryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or di-(C1-C30)alkylamino, a mono- or di- (C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl, a (C1-C30)alkyl(C6-C30)arylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl.

3. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 2, 3, 4, 5, 6 and 7:

4. The organic electroluminescent compound according to claim 1, wherein

X₁, X₂, X₃, X₄, X₅, X₆, X₇, X₈, X₉, X₁₀, X₁₁, X₁₂ and X₁₃ each independently represent N or CR₁;

L represents a single bond, a substituted or unsubstituted (C6-C15)arylene, or a substituted or unsubstituted 5- to 15-membered heteroarylene;

Ar represents hydrogen, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted 5- to 20-membered heteroaryl, or a substituted or unsubstituted di(C6-C15)arylamino, and

R₁ represents hydrogen, or a substituted or unsubstituted di(C6-C15)arylamino;

or is linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (C3-C15) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.

5. The organic electroluminescent compound according to claim 1, wherein

X₁, X₂, X₃, X₄, X₅, X₆, X₇, X₈, X₉, X₁₀, X₁₁, X₁₂ and X₁₃ each independently represent N or CR₁;

L represents a single bond, an unsubstituted (C6-C15)arylene, or an unsubstituted 5- to 15-membered heteroarylene;

Ar represents hydrogen;

an unsubstituted (C6-C20)aryl;

a 5- to 20-membered heteroaryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C25)aryl, a 5- to 20-membered heteroaryl, or a (C1-C6)alkyl(C6-C15)aryl;

or an unsubstituted di(C6-C15)arylamino; and

R₁ represents hydrogen, or a di(C6-C15)arylamino unsubstituted or substituted with a (C1-C6)alkyl;

or is linked to an adjacent substituent to form an unsubstituted monocyclic (C3-C15) aromatic ring.

6. The organic electroluminescent compound according to claim 1, wherein Ar is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted benzofuranyl.

7. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:

8. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.

9. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

10. A display device comprising the organic electroluminescent compound according to claim 1.