IP Library › Granted Patent US 12,029,115
Granted Patent B2
US 12,029,115 · App. 17/251,344 · Granted Jul 2, 2024

Organic light-emitting device

Inventors: Dong Uk Heo (Daejeon, KR); Sung Kil Hong (Daejeon, KR); Jungoh Huh (Daejeon, KR); Miyeon Han (Daejeon, KR); Jae Tak Lee (Daejeon, KR); Junghoon Yang (Daejeon, KR); Heekyung Yun (Daejeon, KR)
Assignee: LG CHEM, LTD.
H10K85/654C07D213/16C07D251/24C07D405/04C07D405/10C07D487/04C07D495/04C09K11/06H10K85/615H10K85/624H10K85/657H10K85/6572H10K85/6574C09K2211/1018H10K50/11H10K50/13H10K50/18H10K2101/10
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Quick Facts
Patent No.
US 12,029,115
App. No.
17/251,344
Granted
Jul 2, 2024
Kind
B2
Abstract

Provided is an organic light emitting device including a first electrode; a second electrode opposite to the first electrode; and a first organic material layer and a second organic material layer provided between the first electrode and the second electrode, wherein the first organic material layer includes a compound of Chemical Formula 1: wherein: at least one of Xa to Xc is N, and the rest are CR; and Ar2 to Ar4 are each independently a substituted or unsubstituted aryl or heterocyclic group, and the second organic material layer includes a compound of wherein: HAr is a substituted or unsubstituted heterocyclic group including at least one or more Ns; L1 and L2 are each independently a direct bond or a substituted or unsubstituted arylene or divalent heterocyclic group; and Ar1 is a direct bond, —O—, or a substituted or unsubstituted arylene or divalent heterocyclic group.

Claims (126)

1. An organic light emitting device comprising:

a first electrode;

a second electrode provided opposite to the first electrode; and

a first organic material layer and a second organic material layer provided between the first electrode and the second electrode,

wherein the first organic material layer is a hole blocking layer or an electron control layer and includes a compound of the following Chemical Formula 1,

the second organic material layer includes a compound of the following Chemical Formula 2, and

a dipole moment value of the second organic material layer is larger than a dipole moment value of the first organic material layer:

wherein in Chemical Formula 1:

at least one of Xa to Xc is N, and the rest are CR;

R is hydrogen, deuterium, a cyano group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and

Ar2 to Ar4 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;

wherein in Chemical Formula 2:

HAr is a substituted or unsubstituted heterocyclic group including one or more Ns;

L1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;

Ar1 is a direct bond, —O—, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;

a to c are each an integer of 1 to 3; and

when a to c are each 2 or greater, the structures in the two or more parentheses are the same as or different from each other.

2. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is the following Chemical Formula 101:

wherein in Chemical Formula 101:

Ar2 to Ar4 have the same definitions as in Chemical Formula 1.

3. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is any one of the following Chemical Formulae 1-1 to 1-3:

wherein in Chemical Formulae 1-1 to 1-3:

Xa to Xc, Ar2 and Ar3 have the same definitions as in Chemical Formula 1;

L is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylylene, or substituted or unsubstituted terphenylene;

R3, R4, R11, R12, R21 and R22 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylphosphine group, or a substituted or unsubstituted phosphine oxide group, or bond to adjacent groups to form a substituted or unsubstituted ring;

X1 and X2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted arylphosphine group, or a substituted or unsubstituted phosphine oxide group, or bond to adjacent groups to form a substituted or unsubstituted ring;

r11 and r12 are the same as or different from each other, and each independently is an integer of 0 to 5;

r21 and r22 are the same as or different from each other, and each independently is an integer of 0 to 4;

m is an integer of 1 to 3;

d is an integer of 1 to 3;

e is an integer of 1 to 4; and

when r11, r12, r21, r22, m, d and e are each 2 or greater, structures in the parentheses are the same as or different from each other.

4. The organic light emitting device of claim 1 , wherein Chemical Formula 1 is any one of the following Chemical Formulae 1-4 to 1-6:

wherein in Chemical Formulae 1-4 to 1-6:

Ar2 and Ar3 have the same definitions as in Chemical Formula 1;

L is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylylene, or substituted or unsubstituted terphenylene;

R3, R4, R11, R12, R21 and R22 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylphosphine group, or a substituted or unsubstituted phosphine oxide group, or bond to adjacent groups to form a substituted or unsubstituted ring;

X1 and X2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted arylphosphine group, or a substituted or unsubstituted phosphine oxide group, or bond to adjacent groups to form a substituted or unsubstituted ring;

r11 and r12 are the same as or different from each other, and each independently is an integer of 0 to 5;

r21 and r22 are the same as or different from each other, and each independently is an integer of 0 to 4;

m is an integer of 1 to 3;

d is an integer of 1 to 3;

e is an integer of 1 to 4; and

when r11, r12, r21, r22, m, d and e are each 2 or greater, structures in the parentheses are the same as or different from each other.

5. The organic light emitting device of claim 1 , wherein Ar2 to Ar4 are the same as or different from each other, and each independently is —L11-Ar11;

the L11s are the same as or different from each other, and each independently is a direct bond or a substituted or unsubstituted arylene group; and

the Ar11s are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

6. The organic light emitting device claim 1 , wherein HAr is the following Chemical Formula 2-1:

wherein in Chemical Formula 2-1:

Ar5 and Ar6 are a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or bond to adjacent groups to form a ring; and

at least one of Xd to Xf is N, and the rest are CH.

7. The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 1 is selected from among the following compounds:

8. The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 2 is selected from among the following compounds:

9. The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 1 and the compound of Chemical Formula 2 satisfy the following Equation 1:

| P El |>|P Eb |  <Equation 1>

wherein in Equation 1:

|P Eb | means an absolute value of a dipole moment of the compound of Chemical Formula 1; and

|P El | means an absolute value of a dipole moment of the compound of Chemical Formula 2.

10. An organic light emitting device comprising:

a first electrode;

a second electrode provided opposite to the first electrode; and

a first organic material layer and a second organic material layer provided between the first electrode and the second electrode,

wherein the first organic material layer includes a compound of the following Chemical Formula 1,

the second organic material layer is an electron transfer layer and includes a compound of the following Chemical Formula 2, and

a dipole moment value of the second organic material layer is larger than a dipole moment value of the first organic material layer:

wherein in Chemical Formula 1:

at least one of Xa to Xc is N, and the rest are CR;

R is hydrogen, deuterium, a cyano group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and

Ar2 to Ar4 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;

wherein in Chemical Formula 2:

HAr is a substituted or unsubstituted heterocyclic group including one or more Ns;

L1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;

Ar1 is a direct bond, —O—, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;

a to c are each an integer of 1 to 3; and

when a to c are each 2 or greater, the structures in the two or more parentheses are the same as or different from each other.

11. An organic light emitting device comprising:

a first electrode;

a second electrode provided opposite to the first electrode;

two or more light emitting layers between the first electrode and the second electrode, wherein the light emitting layers each independently includes a fluorescent dopant or a phosphorescent dopant; and

a first organic material layer and a second organic material layer provided between the first electrode and the second electrode,

wherein the first organic material layer includes a compound of the following Chemical Formula 1,

the second organic material layer includes a compound of the following Chemical Formula 2, and

a dipole moment value of the second organic material layer is larger than a dipole moment value of the first organic material layer:

wherein in Chemical Formula 1:

at least one of Xa to Xc is N, and the rest are CR;

R is hydrogen, deuterium, a cyano group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and

Ar2 to Ar4 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;

wherein in Chemical Formula 2:

HAr is a substituted or unsubstituted heterocyclic group including one or more Ns;

L1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;

Ar1 is a direct bond, —O—, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;

a to c are each an integer of 1 to 3; and

when a to c are each 2 or greater, the structures in the two or more parentheses are the same as or different from each other.

12. The organic light emitting device of claim 11 , comprising three or more light emitting layers between the first electrode and the second electrode, wherein the light emitting layers each includes a blue fluorescent light emitting layer.

13. The organic light emitting device of claim 12 , wherein the three or more light emitting layers are provided consecutively in a direction from the first electrode to the second electrode direction.

14. The organic light emitting device of claim 11 , wherein:

Chemical Formula 1 is any one of the following Chemical Formulae 1-1 to 1-3:

wherein in Chemical Formulae 1-1 to 1-3:

Xa to Xc, Ar2 and Ar3 have the same definitions as in Chemical Formula 1;

L is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylylene, or substituted or unsubstituted terphenylene;

R3, R4, R11, R12, R21 and R22 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylphosphine group, or a substituted or unsubstituted phosphine oxide group, or bond to adjacent groups to form a substituted or unsubstituted ring;

X1 and X2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted arylphosphine group, or a substituted or unsubstituted phosphine oxide group, or bond to adjacent groups to form a substituted or unsubstituted ring;

r11 and r12 are the same as or different from each other, and each independently is an integer of 0 to 5;

r21 and r22 are the same as or different from each other, and each independently is an integer of 0 to 4;

m is an integer of 1 to 3;

d is an integer of 1 to 3;

e is an integer of 1 to 4; and

when r11, r12, r21, r22, m, d and e are each 2 or greater, structures in the parentheses are the same as or different from each other; and

HAr is the following Chemical Formula 2-1:

wherein in Chemical Formula 2-1:

Ar5 and Ar6 are a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or bond to adjacent groups to form a ring; and

at least one of Xd to Xf is N, and the rest are CH.

15. The organic light emitting device of claim 11 , wherein the compound of Chemical Formula 1 is selected from among the following compounds:

16. The organic light emitting device of claim 11 , wherein the compound of Chemical Formula 2 is selected from among the following compounds:

17. The organic light emitting device of claim 11 , wherein the compound of Chemical Formula 1 and the compound of Chemical Formula 2 satisfy the following Equation 1:

| P El |>|P Eb |  <Equation 1>

wherein in Equation 1:

|P Eb | means an absolute value of a dipole moment of the compound of Chemical Formula 1; and

|P El | means an absolute value of a dipole moment of the compound of Chemical Formula 2.

18. The organic light emitting device of claim 10 , wherein the compound of Chemical Formula 1 is selected from among the following compounds:

19. The organic light emitting device of claim 10 , wherein the compound of Chemical Formula 2 is selected from among the following compounds:

20. The organic light emitting device of claim 10 , wherein the compound of Chemical Formula 1 and the compound of Chemical Formula 2 satisfy the following Equation 1:

| P El |>|P Eb |  <Equation 1>

wherein in Equation 1:

|P Eb | means an absolute value of a dipole moment of the compound of Chemical Formula 1; and

|P El | means an absolute value of a dipole moment of the compound of Chemical Formula 2.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2020
From: HEO, DONG UK; HONG, SUNG KIL; HUH, JUNGOH; HAN, MIYEON; LEE, JAE TAK; YANG, JUNGHOON; YUN, HEEKYUNG
To: LG CHEM, LTD.
Reel/Frame 054615/0295 →
Priority Claims (1)
KR 10-2018-0104688 · Sep 3, 2018 · national
Continuity (1)
Related Publication 20210305516A1 · Sep 30, 2021