IP Library Granted Patent US 9,806,271
Granted Patent B2
US 9,806,271 · App. 15/325,140 · Granted Oct 31, 2017

Organic electroluminescent compound and organic electroluminescent device comprising the same

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Quick Facts
Patent No.
US 9,806,271
App. No.
15/325,140
Granted
Oct 31, 2017
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound of Formula 1 (variables Y 1 , Y 2 and R 1 to R 4 defined herein), and an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present disclosure can be used for the manufacture of an organic electroluminescent device showing improvement in luminous efficiency, especially in current efficiency.

Claims (27)

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

wherein Y 1 and Y 2 , each independently, represent NR 11 , CR 12 R 13 , O, or S; with the proviso that at least one of Y 1 and Y 2 represents NR 11 ;

R 11 represents *-L 1 -Ar;

* represents a bonding site;

L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;

Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;

R 12 and R 13 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, (C3-C30), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

R 1 and R 3 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, (C3-C30), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

R 2 and R 4 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;

a and c, each independently, represent an integer of 1 to 4; where a or c is an integer of 2 or more, each of R 1 or R 3 may be the same or different;

b and d, each independently, represent an integer of 1 to 2; where b or d is an integer of 2 or more, each of R 2 or R 4 may be the same or different; and

the heteroaryl(ene) and heterocycloalkyl, each independently, contain at least one hetero atom selected from B, N, O, S, Si, and P.

2. The organic electroluminescent compound according to claim 1 , wherein the substituents for the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, and the substituted mono- or polycyclic, alicyclic or aromatic ring in L 1 , Ar, R 12 , R 13 , and R 1 to R 4 , each independently, are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a (C1-C30)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 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a 3- 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, 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 at least one of Y 1 and Y 2 represents NR 11 in which L 1 represents a single bond or a substituted or unsubstituted (C6-C21)arylene and Ar represents a substituted or unsubstituted 5- to 30-membered heteroaryl.

4. The organic electroluminescent compound according to claim 1 , wherein one of Y 1 and Y 2 is NR 11a and the other is NR 11b , CR 12 R 13 , O, or S;

R 11a represents *-L 1a -Ar a ; R 11b represents *-L 1b -Ar b ;

L 1a and L 1b , each independently, represent a single bond or a substituted or unsubstituted (C6-C21)arylene;

Ar a represents a substituted or unsubstituted 5- to 30-membered heteroaryl;

Ar b represents a substituted or unsubstituted (C6-C30)aryl; and

R 12 and R 13 , each independently, represent a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, (C3-C30), mono- or polycyclic aromatic ring.

5. The organic electroluminescent compound according to claim 4 , wherein L 1a represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene; Ar a represents a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl.

6. The organic electroluminescent compound according to claim 5 , wherein Ar a is selected from the following formulae 2-1 to 2-7:

wherein R 21 to R 27 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a (C1-C30)alkyl, a (C3-C30)cycloalkyl, a (C6-C30)aryl unsubstituted or substituted with a halogen, a cyano, a (C1-C30)alkyl, a 5- to 18-membered heteroaryl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, or a tri(C6-C30)arylsilyl, a 5- to 30-membered heteroaryl unsubstituted or substituted with a halogen, a cyano, a (C1-C30)alkyl, a (C6-C18)aryl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, or a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, or a tri(C6-C30)arylsilyl;

f represents an integer of 1 to 4; g represents an integer of 1 to 3; h represents an integer of 1 to 2; i represents an integer of 1 to 6; j, k, and m, each independently, represent an integer of 1 to 5; where f, g, h, i, j, k, or m is an integer of 2 or more, each of R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , or R 27 may be the same or different; and

the heteroaryl contains at least one hetero atom selected from N, O, and S.

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 device comprising the organic electroluminescent compound according to claim 1 .

Assignments (2)
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2017
From: LEE, MI-JA; KIM, BIT-NA-RI; KIM, NAM-KYUN; KANG, HEE-RYONG
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 043640/0530 →