IP Library › Granted Patent US 11,588,116
Granted Patent B2
US 11,588,116 · App. 17/624,921 · Granted Feb 21, 2023

Organic light emitting device

Inventors: Sang Duk Suh (Daejeon, KR); Min Woo Jung (Daejeon, KR); Jungha Lee (Daejeon, KR); Su Jin Han (Daejeon, KR); Seulchan Park (Daejeon, KR); Sunghyun Hwang (Daejeon, KR); Dong Hoon Lee (Daejeon, KR)
Assignee: LG CHEM, LTD.
H01L51/0072C07D209/86C07D405/14C07D487/04C09K11/06H01L51/0052H01L51/0067H01L51/0073H01L51/0074C07B2200/05C09K2211/1018H01L51/5012H01L2251/5384H01L2251/552
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Quick Facts
Patent No.
US 11,588,116
App. No.
17/624,921
Granted
Feb 21, 2023
Kind
B2
Abstract

Provided is an organic light-emitting device comprising an anode, a cathode, and a light-emitting layer provided between the anode and the cathode, wherein the light-emitting layer comprises a first compound of Chemical Formula 1 and a second compound of Chemical Formula 2: wherein: A is Chemical Formula 1a or 1b: Ar 1 and Ar 2 are each independently a C 6-60 aromatic ring or a C 2-60 heteroaromatic ring, and Ar 1 and Ar 2 are unsubstituted, or substituted with C 1-60 alkyl, C 6-60 aryl, or C 2-60 heteroaryl; Ar′ 1 and Ar′ 2 are each independently substituted or unsubstituted C 6-60 aryl or substituted or unsubstituted C 2-60 heteroaryl; provided that a1+b1+c1+d+e+f is 1 or more; or a2+b2+c2+d+e+f is 1 or more; R′ 1 and R′ 2 are each independently hydrogen, deuterium, C 1-60 alkyl, C 6-60 aryl, or C 2-60 heteroaryl; and r and s are each independently 0 to 7.

Claims (106)

1. An organic light emitting device comprising:

an anode;

a cathode provided to face the anode; and

a light emitting layer provided between the anode and the cathode;

wherein the light emitting layer comprises a first compound of the following Chemical Formula 1 and a second compound of the following Chemical Formula 2:

wherein in Chemical Formula 1:

A is the following Chemical Formula 1a or 1b:

wherein in Chemical Formulae 1a and 1b:

a1, a2 and c2 are each independently an integer of 0 to 5;

b1 and c1 are each independently an integer of 0 to 4;

b2 is an integer of 0 to 3; and

Ar 1 and Ar 2 are each independently a C 6-60 aromatic ring or a C 2-60 heteroaromatic ring containing at least one heteroatom of N, O and S;

wherein Ar 1 and Ar 2 are unsubstituted, or substituted with at least one substituent selected from the group consisting of C 1-60 alkyl, C 6-60 aryl, and C 2-60 heteroaryl containing at least one heteroatom of N, O and S;

D is deuterium; and

d, e and f are each independently an integer of 0 to 10,

provided that a1+b1+c1+d+e+f is 1 or more; or a2+b2+c2+d+e+f is 1 or more;

wherein in Chemical Formula 2:

Ar′ 1 and Ar′ 2 are each independently substituted or unsubstituted C 6-60 aryl or substituted or unsubstituted C 2-60 heteroaryl containing at least one heteroatom of N, O and S;

R′ 1 and R′ 2 are each independently hydrogen, deuterium, C 1-60 alkyl, C 6-60 aryl; or C 2-60 heteroaryl containing at least one heteroatom of N, O and S; and

r and s are each independently an integer of 0 to 7.

2. The organic light emitting device of claim 1 ,

wherein the first compound is the following Chemical Formula 1A or 1B;

wherein in Chemical Formula 1A:

Ar 1 and Ar 2 are each independently a benzene ring, a biphenyl ring, a terphenyl ring, a fluorene ring, a carbazole ring, or a dibenzothiophenyl ring,

wherein Ar 1 and Ar 2 are unsubstituted, or substituted with 1 or 2 substituents selected from the group consisting of C 1-10 alkyl and C 6-20 aryl;

a1+b1+c1+d+e+f is 1 to 43; and

a1, b1, c1, d, e, and f are as defined in claim 1 ;

wherein in Chemical Formula 1B:

Ar 1 and Ar 2 are each independently a benzene ring, a biphenyl ring, a terphenyl ring, a fluorene ring, a carbazole ring, or a dibenzothiophenyl ring,

wherein Ar 1 and Ar 2 are unsubstituted, or substituted with 1 or 2 substituents selected from the group consisting of C 1-10 alkyl and C 6-20 aryl;

a2+b2+c2+d+e+f is 1 to 43; and

a2, b2, c2, d, e, and f are as defined in claim 1 .

3. The organic light emitting device of claim 1 ,

wherein Ar 1 is a benzene ring, and Ar 2 -(D) f is any one selected from the group consisting of the following:

wherein in the above:

f1 is an integer of 0 to 5;

f2 is an integer of 0 to 4;

f3 is an integer of 0 to 5;

f4 is an integer of 0 to 7;

f5 is an integer of 0 to 7; and

f6 is an integer of 0 to 5.

4. The organic light emitting device of claim 1 ,

wherein A is any one of Chemical Formulae 1a-1 to 1a-9 and Chemical Formulae 1b-1 to 1b-6:

wherein in Chemical Formulae 1a-1 to 1a-9 and Chemical Formulae 1b-1 to 1b-6;

a1, b1, c1, a2, b2, c2, d, e, and f are as defined in claim 1 .

5. The organic light emitting device of claim 1 ,

wherein the first compound is any one compound selected from the group consisting of the following compounds:

wherein in Chemical Formulae H1-1-1 to H1-1-9:

a1, b1, c1, and d are as defined in Chemical Formula 1,

e and f1 are each independently an integer of 0 to 5,

provided that a1+b1+c1+d+e+f1 is 1 to 33;

wherein in Chemical Formulae H1-1-10 to H1-1-15:

a2, b2, c2, and d are as defined in Chemical Formula 1, and

e and f1 are each independently an integer of 0 to 5,

provided that a2+b2+c2+d+e+f1 is 1 to 33;

wherein in Chemical Formulae H1-2-1 to H1-2-9 and H1-3-1 to H1-3-9:

a1, b1, c1, and d are as defined in Chemical Formula 1,

e is an integer of 0 to 5,

f2 is an integer of 0 to 4,

f3 is an integer of 0 to 5, and

a1+b1+c1+d+e+f2+f3 is 1 to 37;

wherein in Chemical Formulae H1-2-10 to H1-2-15 and H1-3-10 to H1-3-15;

a2, b2, c2, and d are as defined in Chemical Formula 1,

e is an integer of 0 to 5,

f2 is an integer of 0 to 4,

f3 is an integer of 0 to 5, and

a2+b2+c2+d+e+f2+f3 is 1 to 37;

wherein in Chemical Formulae H1-4-1 to H1-4-9, H1-5-1 to H1-5-9, H1-6-1 to H1-6-9, H1-7-1 to H1-7-9, H1-8-1 to H1-8-9, H1-9-1 to H1-9-9, H1-10-1 to H1-10-9, H1-11-1 to H1-11-9, H1-12-1 to H1-12-9, H1-13-1 to H1-13-9, H1-14-1 to H1-14-9, and H1-15-1 to H1-15-9:

a1, b1, c1, and d are as defined in Chemical Formula 1,

e is an integer of 0 to 5,

f4 is an integer of 0 to 7, and

a1+b1+c1+d+e+f4 is 1 to 35;

wherein in Chemical Formulae H1-4-10 to H1-4-15, H1-5-10 to H1-5-15, H1-6-10 to H1-6-15, H1-7-10 to H1-7-15, H1-8-10 to H1-8-15, H1-9-10 to H1-9-15, H1-10-10 to H1-10-15, H1-11-10 to H1-11-15, H1-12-10 to H1-12-15, H1-13-10 to H1-13-15, H1-14-10 to H1-14-15, and H1-15-10 to H1-15-15:

a2, b2, c2, and d are as defined in Chemical Formula 1,

e is an integer of 0 to 5,

f4 is an integer of 0 to 7, and

a2+b2+c2+d+e+f4 is 1 to 35;

wherein in Chemical Formulae H1-16-1 to H1-16-9, H1-17-1 to H1-17-9, H1-18-1 to H1-18-9, and H1-19-1 to H1-19-9:

a1, b1, c1, and d are as defined in Chemical Formula 1,

e is an integer of 0 to 5,

f5 is an integer of 0 to 7,

f6 is an integer of 0 to 5, and

a1+b1+c1+d+e+f5+f6 is 1 to 40;

wherein in Chemical Formulae H1-16-10 to H1-16-15, H1-17-10 to H1-17-15, H1-18-10 to H1-18-15, and H1-19-10 to H1-19-15:

a2, b2, c2, and d are as defined in Chemical Formula 1,

e is an integer of 0 to 5,

f5 is an integer of 0 to 7,

f6 is an integer of 0 to 5, and

a2+b2+c2+d+e+f5+f6 is 1 to 40.

6. The organic light emitting device of claim 1 ,

wherein the second compound is the following Chemical Formula 2′:

wherein in Chemical Formula 2′:

Ar′ 1 , Ar′ 2 , R′ 1 , R′ 2 , r, and s are as defined in claim 1 .

7. The organic light emitting device of claim 1 ,

wherein Ar′ 1 and Ar′ 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl; and

Ar′ 1 is unsubstituted, or substituted with at least one substituent selected from the group consisting of deuterium and C 6-20 aryl.

8. The organic light emitting device of claim 1 ,

wherein at least one of Ar′ 1 and Ar′ 2 is phenyl or biphenylyl.

9. The organic light emitting device of claim 1 ,

wherein R′ 1 and R′ 2 are each independently hydrogen, deuterium, or phenyl.

10. The organic light emitting device of claim 1 ,

wherein r+s is 0 or 1.

11. The organic light emitting device of claim 1 ,

wherein the second compound is any one compound selected from the group consisting of the following compounds:

12. The organic light emitting device of claim 1 ,

wherein the first compound and the second compound are included in the light emitting layer in a weight ratio of 10:90 to 90:10.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2022
From: SUH, SANG DUK; JUNG, MIN WOO; LEE, JUNGHA; HAN, SU JIN; PARK, SEULCHAN; HWANG, SUNGHYUN; LEE, DONG HOON
To: LG CHEM, LTD.
Reel/Frame 058555/0548 →
Priority Claims (1)
KR 10-2020-0030233 · Mar 11, 2020 · national
Continuity (1)
Related Publication 20220310936A1 · Sep 29, 2022