Organic electroluminescent compound and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-9859507-B2
Application number	US-201515306123-A
Country	US
Kind code	B2
Filing date	Apr 30, 2015
Priority date	May 2, 2014
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

The present disclosure relates to an organic electroluminescent compound of Formula 1 (variables R1-R10 defined herein), and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound according to the present disclosure, it is possible to produce an organic electroluminescent device which can be operated at a lowered driving voltage, shows excellence in luminous efficiency such as current efficiency and power efficiency, and has high color purity and improved lifespan.

First claim

The invention claimed is:

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

wherein
X and Y, each independently, represent —CR 12 — or —N—, with the proviso that X and Y are not be simultaneously —CR 12 —, and
R 1 to R 12 , 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 3- to 30-memberedheteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, 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 tri(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 benzene ring or a substituted or unsubstituted naphthalene ring,
wherein the heteroaryl of the substituted or unsubstituted 3- to 30-memberedheteroaryl contains one or more hetero atoms selected from the group consisting of N, O and S.

2. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl, the substituted aryl, the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, and the substituted benzene ring or naphthalene ring in R 1 to R 12 , 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 (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, 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 or a di(C6-C30)arylamino, a (C6-C30)aryl unsubstituted or substituted with a 3- to 30-membered heteroaryl or a di(C6-C30)arylamino, atri(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 the compound of formula 1 is represented by any one of the following formulae 2 to 4:

wherein R 1 to R 12 are as defined in claim 1 .

4. The organic electroluminescent compound according to claim 1 , wherein R 1 to R 12 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or a substituted or unsubstituted di(C6-C20)arylamino, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzenering or a substituted or unsubstituted naphthalene ring.

5. The organic electroluminescent compound according to claim 4 , wherein R 1 to R 12 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, or any one of the following formulae 5-1 to 5-9, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring:

wherein
L a , L b , L c , and L d , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30-membered heteroarylene;
Z represents —S—, —O—, —NR 13 —, or —CR 14 R 15 —;
R 13 to R 15 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted 3- to 7-membered heterocycloalkyl;
R 31 to R 37 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, 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 mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, or a (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, 3- to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur;
a represents an integer of 1 to 3; b to d and f, each independently, represent an integer of 1 to 4; e represents an integer of 1 to 5; where a, b, c, d, e, or f is an integer of 2 or more, each of R 31 , R 32 , R 33 , R 34 , R 35 , or R 36 may be the same or different; and
* represents a bonding site;
wherein the heteroaryl(ene) and heterocycloalkyl, each independently, contain at least one hetero atom(s) selected from the group consisting of N, O and S.

6. The organic electroluminescent compound according to claim 5 , wherein at least one of R 1 to R 7 represents any one of formulae 5-6 to 5-8, and Z of formula 5-6 represents —NR 13 —.

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

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Kang Hee-Ryong
• Kang Hyun-Ju
• Lim Young-Mook
• Lee Mi-Ja
• Kim Nam-Kyun
• Kim Bitnari
• Hong Jin-Ri
• Moon Doo-Hyeon
• Lee Su-Hyun

Classifications

• C09K2211/1033

  with oxygen · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title