Polymer and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-9346912-B2
Application number	US-201213606879-A
Country	US
Kind code	B2
Filing date	Sep 7, 2012
Priority date	Sep 9, 2011
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

A polymer and an organic light-emitting device including the polymer represented by Formula 1

wherein at least one of a first dihedral angle between an A 1 ring of an n th repeating unit and a first aromatic ring of an (n−1) th repeating unit and a second dihedral angle between an A 2 ring of the n th repeating unit and a second aromatic ring of a (n+1) th repeating unit is equal to or greater than an angle of χ 50% represented by Equation 1.

χ 50% =A+B (φ+4θ)  Equation 1

First claim

What is claimed is:

1. A polymer comprising m repeating units,
wherein an n th repeating unit of the m repeating units is a first repeating unit represented by Formula 1 below,
wherein at least one of a first dihedral angle between an A 1 ring of the n th repeating unit and a first aromatic ring of an (n−1) th repeating unit and a second dihedral angle between an A 2 ring of the n th repeating unit and a second aromatic ring of a (n+1) th repeating unit is equal to or greater than an angle of χ 50% represented by Equation 1:
χ 50% =A+B (φ+4θ)  Equation 1

wherein
the first aromatic ring is bound to the A 1 ring by a single bond;
the second aromatic ring is bound to the A 2 ring by a single bond;
R 1 to R 7 of Formula 1 are the same or different in each repeating unit and are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 3 -C 60 cycloal kenyl group, a substituted or unsubstituted C 2 -C 60 cycloalkynyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 2 -C 60 heterocycloalkynyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, an isocyanate group, a (meth)acrylate group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 6 ) (wherein Q i to Q 5 are each independently a hydrogen, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 3 -C 60 cycloalkyl group, a C 6 -C 60 aryl group, a C 2 -C 60 heteroaryl group, or a combination thereof), -(Q 6 )O(Q 7 ) (wherein Q 6 is a substituted or unsubstituted C 1 -C 60 alkylene group and Q 7 is a hydrogen or a substituted or unsubstituted C 1 -C 60 alkyl group), or a combination thereof;
X of Formula 1 is the same or different in each repeating unit and is each independently absent, or a linker comprising a C 1 -C 7 substituted or unsubstituted alkylene group or a Group 16 element;
m is an integer from 2 to 1000;
n is a variable from 2 to m−1;
A of Equation 1 is 26.03, and B is 0.0445;
φ of Equation 1 is an angle between the A 1 ring and A 2 ring of Formula 1, as illustrated in Formula 1-1 below; and
θ of Equation 1 is an angle between a first imaginary line extending from a bond between the A 1 ring and a A 3 ring of Formula 1 in a direction close to nitrogen of the A 3 ring and a second imaginary line extending from a bond between the A 2 ring and A 3 ring in a direction close to the nitrogen of the A 3 ring, as illustrated in Formula 1-2 below

wherein the first dihedral angle, the second dihedral angle, φ of Equation 1, and θ of Equation 1 are calculated by application of density functional theory with a B3LYP/6-31+G(D) basis set, and
wherein the polymer further comprises a second repeating unit represented by Formula 5A, 5B, 5D, or 5E:

wherein, in Formulae 5A, 5B, 5D, and 5E,
R 21 and R 22 are each independently a substituted or unsubstituted C 1 -C 60 alkyl group; and
Y 1 to Y 4 are each independently a hydrogen, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, or a combination thereof.

2. The polymer of claim 1 , wherein X is the linker represented by Formula 2-2 below; 158.37≦φ≦160.37; 32.52≦θ≦34.52; and 38.00≦χ 50% ≦40.00:

wherein R 11 to R 14 of Formula 2-2 are each independently a hydrogen, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 3 -C 60 cycloalkenyl group, a substituted or unsubstituted C 2 -C 60 cycloalkynyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 2 -C 60 heterocycloalkynyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, an isocyanate group, a (meth)acrylate group, or a combination thereof.

3. The polymer of claim 2 , wherein R 11 to R 14 of Formula 2-2 are each independently a hydrogen atom; a deuterium atom; F; Cl; a hydroxyl group; a cyano group; a nitro group; a carboxyl group; a methyl group; an ethyl group; a propyl group; an i-propyl group; a butyl group; an i-butyl group; a t-butyl group; a pentyl group;
a hexyl group; a heptyl group; an octyl group; a 2-ethylhexyl group; a nonyl group; a decyl group; a 3,7-dimethyloctyl group; a methoxy group; an ethoxy group; a propyloxy group; an i-propyloxy group; a butoxy group; an i-butoxy group; a t-butoxy group; a pentyloxy group; a hexyloxy group; a heptyloxy group; an octyloxy group; a 2-ethylhexyloxy group; a nonyloxy group; a decyloxy group; a 3,7-dimethyloctyloxy group;
or a substituted group that is a methyl group, an ethyl group, a propyl group, an i-propyl group, a butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, 3,7-dimethyloctyl group, a methoxy group, an ethoxy group, a propyloxy group, an i-propyloxy group, a butoxy group, a i-butoxy group, a t-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, or a 3,7-dimethyloctyloxy group that are each substituted with a deuterium atom, —F, —Cl, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, or a combination thereof.

4. The polymer of claim 1 , wherein X is absent; φ=180.00; −34.45≦θ≦−32.45; and 27.00≦χ 50% ≦29.00.

5. The polymer of claim 1 , wherein X is the linker represented by the Group 16 element —O—; 167.18≦φ≦169.18; −2.81≦θ≦0.81; and 32.00≦χ 50% ≦34.00.

6. The polymer of claim 1 , wherein X is the linker represented by the Group 16 element —S—; 149.27≦φ≦151.27; 10.01≦θ≦12.01; and 34.00≦χ 50% ≦36.00.

7. The polymer of claim 1 , wherein X is the linker represented by the Group 16 element —Se—; 145.94≦φ≦147.94; 14.46≦θ≦16.46; and 34.00≦χ 50% ≦36.00.

8. The polymer of claim 1 , wherein, in Formula 1, R 2 to R 7 are each a hydrogen

Assignees

• Choi Hyeon-Ho
• Son Jhun-Mo
• Kang Ho-Suk
• Yang Hye-Yeon
• Jung Yong-Sik
• Samsung Electronics Co Ltd

Inventors

• Choi Hyeon-Ho
• Son Jhun-Mo
• Kang Ho-Suk
• Yang Hye-Yeon
• Jung Yong-Sik

Classifications

• H01L51/0067

  Electricity · mapped topic

• H01L51/0043

  Electricity · mapped topic

• C08G61/124

  with a five-membered ring containing one nitrogen atom in the ring · CPC title

• H01L51/0085

  Electricity · mapped topic

• C08G2261/3142

  fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene · CPC title