IP Library Granted Patent US 10,454,044
Granted Patent B2
US 10,454,044 · App. 15/774,288 · Granted Oct 22, 2019

Plurality of host materials and organic electroluminescent device comprising the same

Inventors: Young-Mook Lim (Yongin, KR); Bitnari Kim (Suwon, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
H01L51/0072C07D209/08C07D209/86C07D403/10C07D491/048C07D495/04H01L51/0059H01L51/0067H01L51/5016H01L2251/5384
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Quick Facts
Patent No.
US 10,454,044
App. No.
15/774,288
Granted
Oct 22, 2019
Kind
B2
Abstract

The present disclosure relates to a host material and an organic electroluminescent device comprising the same. By using a specific combination of two or more host compounds according to the present disclosure, the organic electroluminescent device of the present disclosure has luminous efficiency at least equivalent to or higher than conventional devices and has lifespan better than conventional devices.

Claims (38)

1. A host material that comprises one or more first host compounds and one or more second host compounds wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2:

wherein

L 1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene,

A represents hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzofuranyl,

Ar 1 , Ar 2 , and Ar 3 , each independently, represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3- to 30-membered heteroaryl(ene); or Ar 2 and Ar 3 may be linked to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur,

R 1 represents deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R 1 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, or a combination of the alicyclic ring and the aromatic ring,

wherein the heteroaryl(ene) contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P,

a represents an integer of 0 to 4,

and when a is an integer of 2 or more, each of R 1 may be the same or different;

wherein

Ar 4 and Ar 5 , each independently, represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted 3- to 30-membered heteroaryl,

R 3 and R 4 , each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino,

wherein the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and

c represents an integer of 0 to 4; d represents an integer of 0 to 6; and when c or d is an integer of 2 or more, each of R 3 or R 4 may be the same or different.

2. The host material according to claim 1 , wherein formula 2 is represented by any one of the following formulae 12 to 16:

wherein Ar 4 , Ar 5 , R 3 , R 4 , c, and d are as defined in claim 1 .

3. The host material according to claim 1 , wherein the first host compound of formula 1 is selected from the group consisting of:

4. The host material according to claim 1 , wherein the second host compound of formula 2 is selected from the group consisting of:

5. The host material according to claim 1 , wherein formula 1 is represented by any one of the following formulae 3 to 7:

wherein

Ar 1 , Ar 2 , and Ar 3 , each independently, represent a substituted or unsubstituted (C6-C30)aryl(ene), or a substituted or unsubstituted 3 to 30-membered heteroaryl(ene);

X represents S, O or CR 7 R 8 ;

R 2 and R 5 to R 8 , each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R 2 and R 5 to R 8 , each independently, are linked to an adjacent substituent(s) to form a substituted or unsubstituted 3 to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;

b and f, each independently, represent an integer of 0 to 4, and e represents an integer of 0 to 2; when each of b or f represents an integer of 2 or more, or when e represents an integer of 2, each of R 2 , R 5 , or R 6 may be the same or different; and

L 1 , R 1 , and a are as defined in claim 1 .

6. The host material according to claim 5 , wherein formula 3 is represented by any one of the following formulae 8 to 10:

wherein

R 9 to R 12 , each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R 9 to R 12 , each independently, 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, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;

the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P;

g and h, each independently, represent an integer of 0 to 6; i represents an integer of 0 to 4; j represents an integer of 0 to 7; when each of g, h, i or j represents an integer of 2 or more, each of R 9 , R 10 , R 11 or R 12 may be the same or different; and

L 1 , R 1 , R 2 , Ar 1 , Ar 2 , Ar 3 , a, and b are as defined in claim 5 .

7. The host material according to claim 5 , wherein formula 4 is represented by the following formula 11:

wherein

R 13 and R 14 , each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or R 13 and R 14 , each independently, 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, or a combination of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;

the heteroaryl contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P;

k represents an integer of 0 to 4, and m represents an integer of 0 to 7; when each of k or m represents an integer of 2 or more, each of R 13 or R 14 may be the same or different; and

L 1 , R 1 , R 5 , R 6 , Ar 1 , Ar 3 , a, e, and f are as defined in claim 5 .

8. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer disposed between the anode and cathode, wherein the light-emitting layer comprises a host and a dopant, and the host comprises the host material according to claim 1 .

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2022
From: SHI, RUI
To: DOW CHEMICAL(CHINA) INVESTMENT COMPANY LIMITED
Reel/Frame 058857/0866 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2022
From: QU, ZHAOHUI
To: ROHM AND HAAS COMPANY
Reel/Frame 058857/0960 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2022
From: DOW CHEMICAL (CHINA) INVESTMENT COMPANY LIMITED
To: THE DOW CHEMICAL COMPANY
Reel/Frame 058858/0027 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2022
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 058858/0184 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2019
From: LIM, YOUNG MOOK; KIM, BITNARI
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 051005/0143 →
Priority Claims (2)
KR 10-2015-0161209 · Nov 17, 2015 · national
KR 10-2016-0120026 · Sep 20, 2016 · national
Continuity (1)
Related Publication 20190074448A1 · Mar 7, 2019